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US 12,520,844 B2Granted
Triazine and pyrimidine (thio)amides as fungicidal compounds
AssigneeBayer Aktiengesellschaft
InventorsJulie Geist, Cyril Montagne, Lionel Nicolas, Valerie Toquin, Mathieu Gourgues, Vincent Thomas, Mazen Es-Sayed
Life of this patent
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Abstract
The present disclosure relates to triazine and pyrimidine (thio)amide compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.
Claims11
A compound of formula (I)
- or a salt or N-oxide thereof, or a solvate of the salt or N-oxide thereof,
- wherein
- A is N or C—R8,
- wherein
- R8 is hydrogen, halogen, cyano or C1-C4-alkyl,
- T is O or S,
- n is 0 or 1,
- m is 0 or 1,
- 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-cyclo-alkyl-ring or a 3- to 7-membered heterocyclyl-ring,
- and
- R3 and RS are independently hydrogen or halogen,
- or
- 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-haloatkylsulfinyl, 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 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, and
- Q is C6-C14-aryl, C3-C12-carbocycle, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl,
- wherein C6-C14-aryl, C3-C12-carbocycle, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted by one to five Qs substituents 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, 5- to 14-membered heteroaryl, —O—Si(C1-C6-alkyl)3, —Si(C1-C6-alkyl)3, —O—C(═O)R33, —NR34C(═O)R31, —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 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.
73 more elements
Dependencies are inferred from the claim text.