Heterocyclyl pyrimidines and triazines as novel fungicides

Patent metadata

Field	Value
Publication number	US-12565489-B2
Application number	US-202118008116-A
Country	US
Kind code	B2
Filing date	Jun 1, 2021
Priority date	Jun 4, 2020
Publication date	Mar 3, 2026
Grant date	Mar 3, 2026

Abstract

The present disclosure relates to heterocyclyl pyrimidine and heterocyclyl triazine compounds, processes and intermediates for their preparation as well as the uses thereof for controlling phytopathogenic microorganisms, such as phytopathogenic fungi.

First claim

The invention claimed is:

1 . A compound of formula (I):

wherein
A 1 is N or CR 8 ,
wherein
R 8 is hydrogen, halogen, cyano or C 1 -C 4 -alkyl,

A 2 is O, S, C(═O), S(═O), S(═O) 2 , NR 1 or CR 2A R R2B ,
wherein
R 1 is hydrogen, formyl, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and
wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cyclo-alkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

R 2A and R 2B are independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and
wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 5 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

or
R 2A and R 2B form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,

m is 0, 1 or 2,
T is hydrogen, hydroxyl, C 1 -C 6 -alkyl, —C(═O)R 11 , —C(═O)(OR 12 ), —C(═O)N(R 13 ) 2 , —S(═O)R 14 , —S(═O) 2 R 14 or —S(═O) 2 N(R 14 ) 2 ,
wherein
R 11 and R 12 are independently C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl,
R 13 and R 14 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl,

R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkyl-carbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and
wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halo-alkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

and
wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,

or
R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 )—, —C(═NR L8 )— or a group of formula

wherein
said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA ,
# is the point of attachment to the heterocyclyl-moiety,
## is the point of attachment to R 6 ,
L 1 is a direct bond or C 1 -C 6 -alkylene,
L 2 is a direct bond or C 1 -C 6 -alkylene,
E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC ,

R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl,
R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl,
wherein
L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,

and/or
two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
L SC is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy,

Assignees

• Bayer Ag

Inventors

• Geist Julie
• Millet Anthony
• Montagne Cyril
• Nicolas Lionel
• Tsuchiya Tomoki
• Thomas Vincent

Classifications

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title