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US 2023/0348392 A1Published application
Pyridine (thio)amides as fungicidal compounds
AssigneeBayer Aktiengesellschaft
InventorsJulie GEIST, Anthony MILLET, Anne-Sophie REBSTOCK, Cyril MONTAGNE, Lionel NICOLAS, Valerie TOQUIN, Mathieu GOURGUES, Dominique LOQUE, Vincent THOMAS, Mazen ES-SAYED (DECEASED), Alexander SUDAU
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Abstract
The present disclosure relates to pyridine (thio)amide compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.
Claims14
A compound of formula (I)
- or a salt, N-oxide, or solvate thereof, wherein
- T is O or S,
- n is 0 or 1,
- m is 0 or 1,
- provided that when n is 0 and m is 0, then R6 is C1-C3-alkoxy or C1-C3-haloalkoxy, wherein C1-C3-alkoxy or C1-C3-haloalkoxy are substituted as defined for R6,
- R1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, —C(═O)R10, —C(═O)(OR11), —S(═O)R12, —S(═O)2R12, —C(═O)N(R13)2 or —S(═O)2N(R14)2,
- wherein
- R10, R11 and R12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,
- R13 and R14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,
- R2 and R3 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl, or
- R2 and R3 form together with the carbon atom to which they are attached to a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
- R4 and R5 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl, or
- R4 and R5 form together with the carbon atom to which they are attached to a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, or
- R2 and R4 form together with the carbon atom to which they are attached to a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, and
- R3 and R5 are independently hydrogen or halogen, or
- R2 and R4 form together a group of formula **—C(R3)═C(R5)—##,
- wherein
- ** is the point of attachment to N(R1),
- ## is the point of attachment to R6, and
- R3 and R5 are independently hydrogen or C1-C6-alkyl,
- R6 is C3-C12-carbocycle, C6-C14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C12-carbocyclyloxy, C6-C14-aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C1-C3-alkoxy or C1-C3-haloalkoxy,
- wherein C1-C3-alkoxy and C1-C3-haloalkoxy are independently substituted with one substituent selected from the group consisting of C3-C12-carbocycle, C6-C14-aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
- wherein said C3-C12-carbocycle, C6-C14-aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R6S substituents,
- wherein C3-C12-carbocycle, C6-C14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C12-carbocyclyloxy, C6-C14-aryloxy, 5- to 14-membered heteroaryloxy and 3- to 14-membered heterocyclyloxy are optionally substituted with one to four R6S substituents,
- wherein
- R6S is independently halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R15)2, —C(═O)R16, —C(═O)(OR17), —C(═O)N(R18)2, —S(═O)2N(R19)2, —O—Si(C1-C6-alkyl)3 or —Si(C1-C6-alkyl)3,
- wherein said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3 and —Si(C1-C6-alkyl)3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl, and
- wherein said C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C14-aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substitutents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl, or
- two substituents C1-C6-alkyl attached to the same carbon atom form a C3-C8-cycloalkyl-ring, or
- two R6S substituents optionally form together with the carbon atom to which they are attached to a C3-C8-cycloalkyl-ring,
- and wherein
- R15 is hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,
- wherein said C1-C6-alkyl is furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl, and
- wherein said C3-C8-cycloalkyl is furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
- R16, R17, R18 and R19 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,
- wherein said C1-C6-alkyl or C1-C6-haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl,
- R7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C3-C8-cycloalkoxy, C6-C14-aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(R20)2, —C(═NR21)R22, —NR23C(═O)R24, —C(═O)(OR25), —C(═O)N(R26)2, —S(═O)2N(R27)2 or —S(═O)(═NR28)R29,
- wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted with one to three R7Sa substituents,
- wherein C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C3-C8-cycloalkoxy, C6-C14-aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R7Sc substituents,
- and wherein
- R20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
- wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted with one to three substituents R7Sa, and
- wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substitutents R7Sc,
- R21 and R22 are independently hydrogen, hydroxyl, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino,
- wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino are optionally substituted with one to three R7Sa substituents,
- R23, R24, R25, R26, R27, R28 and R29 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,
- wherein C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with one to three R7Sa substituents, and
- wherein C3-C8-cycloalkyl is optionally substituted with one to three R7Sc substituents,
- wherein
- R7Sa is independently cyano, hydroxyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, C6-C14-aryl or 3- to 7-membered heterocyclyl,
- R7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 or 3- to 7-membered heterocyclyl, or
- two R7Sc substituents C1-C6-alkyl that are bound to the same carbon atom form together a C3-C8-cycloalkyl,
- R8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C14-aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —N(R30)2, —SR31, —S(═O)R31 or —S(═O)2R31,
- wherein
- said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3 and —Si(C1-C6-alkyl)3 are optionally substituted with one to three R8Sa substituents,
- said C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C14-aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C14-aryloxy and 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R8Sc substituents,
- and wherein
- R30 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
- wherein
- said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl in turn are optionally substituted with one to three R8Sa substituents,
- said C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R8Sc substituents,
- R31 is C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
- wherein
- said C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl in turn are optionally substituted with one to three R8Sa substituents,
- said C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C14-aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R8Sc substituents,
- and wherein
- R8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, 3- to 7-membered heterocyclyl and —N(R32)2,
- wherein
- said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C1-C6-alkyl substituents that may be identical or different,
- R32 is hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C1-C6-alkylcarbonyl,
- R8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —O—Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,
- wherein
- said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C1-C6-alkyl that may be identical or different, or
- two R8Sc substituents optionally form together with the carbon atom to which they are attached to a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
- wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C1-C6-alkyl that may be identical or different,
- R9 is hydrogen, halogen, cyano or C1-C4-alkyl, and
- Q is phenyl, azulenyl, naphthyl, C3-C12-carbocycle, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl,
- wherein phenyl is substituted by one to five substituents QS, and
- wherein azulenyl, naphthyl, C3-C12-carbocycle, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted by one to five substituents QS,
- wherein
- QS is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, phenyl, naphthyl, 5- to 14-membered heteroaryl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —O—C(═O)R33, —NR34C(═O)R35, —C(═O)N(R36)2, —C(═S)R37, —C(═S)N(R38)2, —C(═NR39)R40, —C(═NOR41)R42 and —N(R43)2,
- wherein
- said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, —O—Si(C1-C6-alkyl)3 and —Si(C1-C6-alkyl)3 are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,
- said C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, phenyl, napthyl and 5- to 14-membered heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclyl,
- wherein said C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C3-C8-cycloalkyl,
- R34, R35, R36 R37 R38 R39 R40 R41 and R42 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,
- wherein
- said C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,
- and wherein
- R43 is independently hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,
- wherein said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, —Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,
- wherein said C3-C8-cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclyl,
- wherein said C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C3-C8-cycloalkyl,
- provided that the compound of formula (I) is not
- 3-chloro-N-[4-(methylsulfanyl)benzyl]-5-(tetrahydrofuran-2-yloxy)isonicotinamide.
92 more elements
(canceled)
A compound of formula (3),
- wherein
- n is 1,
- m is 1,
- R1 is hydrogen,
- R2 and R3 are hydrogen,
- R4 and R5 are independently hydrogen or fluorine,
- provided that at least one of R4 and R5 is not hydrogen,
- R6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, phenyloxy or benzyloxy,
- wherein phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, phenyloxy and benzyloxy are optionally substituted with one to three R6S substituents,
- wherein
- R6S is independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, —C(═O)R16 or —C(═O)(OR17),
- wherein said C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridinyl are optionally furthermore substituted with one or two substitutents independently selected from the group consisting of fluoro, chloro, C1-C4-alkyl and C1-C4-haloalkyl,
- and wherein
- R16 is C1-C4-alkyl,
- R17 is hydrogen or C1-C4-alkyl,
- R7 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, —N(R20)2, —C(═NR21)R22 or —C(═O)(OR5),
- wherein C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted with one or two R7Sa substituents,
- wherein C3-C6-cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted with one or two R7Sc substituents,
- wherein
- R20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,
- R21 is C1-C4-alkyl or C1-C4-alkoxy,
- R22 is C1-C4-alkyl,
- R25 is hydrogen or C1-C4-alkyl,
- and wherein
- R7Sa is independently C1-C4-alkoxy or phenyl,
- R7Sc is independently halogen or C1-C4-alkyl,
- R8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylsulfanyl, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridinyl or —N(R30)2,
- wherein said C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are optionally substituted with one or two R8Sc substituents,
- R30 is C1-C6-alkyl,
- R8Sc is independently halogen or C1-C4-alkyl,
- R9 is hydrogen or halogen, and
- X is halogen,
- provided that the compound of formula (3) is not:
- 5-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-2-(trifluoromethyl)isonicotinamide (1918165-74-8),
- 3-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide (1918165-35-1);
- or
- 3-bromo-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide (1918165-33-9).
34 more elements
A compound of formula (1)
- wherein
- Q is naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridinyl, quinolinyl or a group of formula
- wherein
- § 2 is the attachment to the oxygen atom,
- QS1 is hydrogen or halogen,
- QS2 is hydrogen, halogen, cyano, nitro, C1-C4-alkyl, trifluoromethyl, difluoromethyl, C1-C4-alkylcarbonyl, C1-C6-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkynyl, C3-C6-cycloalkyl, oxiranyl or oxetanyl,
- with the provisio that at least one of QS1 and QS2 is different from hydrogen. and
- wherein naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridinyl and quinolinyl are optionally substituted by one to three substituents QS,
- wherein
- QS is independently selected from the group consisting of halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylsulfanyl, C3-C6-cycloalkyl, oxetanyl, phenyl, pyrazolyl, pyridinyl and —N(R43)2,
- wherein
- said C1-C4-alkyl and C1-C4-alkoxy are optionally substituted with one or two substituents independently selected from the group consisting of hydroxyl, C1-C4-alkoxy, and C1-C4-alkoxycarbonyl,
- said C3-C6-cycloalkyl, phenyl, pyrazolyl and pyridinyl are optionally substituted with one or two substituents independently selected from the group consisting of halogen and C1-C4-alkyl,
- and wherein
- R43 is hydrogen or C1-C4-alkyl,
- R7 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, —N(R20)2, —C(═NR21)R22 or —C(═O)(OR25),
- wherein C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted with one or two R7Sa substituents,
- wherein C3-C6-cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted with one or two R7Sc substituents,
- wherein
- R20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,
- R21 is C1-C4-alkyl or C1-C4-alkoxy,
- R22 is C1-C4-alkyl,
- R25 is hydrogen or C1-C4-alkyl,
- and wherein
- R7Sa is independently C1-C4-alkoxy or phenyl,
- R7Sc is independently halogen or C1-C4-alkyl,
- R8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylsulfanyl, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridinyl or —N(R30)2,
- wherein said C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are optionally substituted with one or two R8Sc substituents,
- R30 is C1-C6-alkyl,
- R8Sc is independently halogen or C1-C4-alkyl,
- R9 is hydrogen or halogen, and
- U1 is hydroxyl, halogen or C1-C6-alkoxy.
29 more elements
Dependencies are inferred from the claim text.