Pyridazine (THIO)amides as fungicidal compounds

Patent metadata

Field	Value
Publication number	US-12414565-B2
Application number	US-201917297984-A
Country	US
Kind code	B2
Filing date	Nov 27, 2019
Priority date	Nov 28, 2018
Publication date	Sep 16, 2025
Grant date	Sep 16, 2025

Abstract

The present disclosure relates to pyridazine (thio) amide compounds of the formula (I):

wherein T, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and Q are as recited herein as well as their salts, N-oxides, and solvates, 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
T is O or S;
n is 0 or 1;
m is 0 or 1;
provided m is 1 when n is 1;
R 1 is selected from the group consisting of hydrogen, hydroxyl, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, —C(═O)R a1 , —C(═O) (OR a1 ), —S(═O)R a1 , —S(═O) 2 R a1 , —C(═O)N(R a2 ) 2 and S(═O) 2 N(R a2 ) 2 , wherein R a1 is selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, and C 2 -C 6 -alkenyl and R a2 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl and C 2 -C 6 -alkenyl;
R 2 and R 3 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl and C 3 -C 8 -cycloalkyl, or R 2 and R 3 form, together with the carbon atom to which they are attached to, a C 3 -C 8 -cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle;
R 4 and R 5 are independently selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl and C 3 -C 8 -cycloalkyl, or R 4 and R 5 form, together with the carbon atom to which they are attached to, a C 3 -C 8 -cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle; or
R 2 and R 4 form, together with the carbon atom to which they are attached to, a C 3 -C 8 -cycloalkyl or a non-aromatic 3- to 7-membered monocyclic heterocycle, and R 3 and R 5 are independently hydrogen or halogen; or
R 2 and R 4 form together a covalent bond and R 3 and R 5 are independently hydrogen or C 1 -C 6 -alkyl;
R 6 is selected from the group consisting of phenyl, indanyl, 1,2,3,4-tetrahydronaphthalenyl, spiro [cyclopropane-1,2′-indane]-1-yl, naphthyl, 2,3-dihydrobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, furanyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzofuranyl, benzoxazolyl, quinolinyl, isoquinolinyl, imidazo [1,2-a]pyridinyl, phenoxy, benzyloxy and —OCF 2 -phenyl, wherein each cyclic, or cyclic moiety of R 6 may be substituted with one or more R 6S that may be the same or different
R 6S is selected from the group consisting of halogen, cyano, 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 2 -C 6 -alkynyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyl, aromatic C 6 -C 14 -carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle, wherein each cyclic R 6S may be substituted independently with one or more halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxycarbonyl;

R 7 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, aromatic C 6 -C 14 -carbocycle, aromatic 5- or 6-membered monocyclic heterocycle, non-aromatic 3- to 7-membered monocyclic heterocycle, C 3 -C 8 -cycloalkyloxy, aromatic C 6 -C 14 -carbocyclyloxy, aromatic 5- or 6-membered monocyclic heterocyclyloxy, non-aromatic 3- to 7-membered monocyclic heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R e ) 2 , —C(═NR f )R f , —NR g C, (═O)R g , —C(═O)(OR g ), —C(═O)N(R 8 ) 2 , —S(═O) 2 N(R g ) 2 and —S(═O)(═NR g )R g ,
wherein R e is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, aromatic C 6 -C 14 -carbocycle, aromatic 5- or 6-membered monocyclic heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein R f is independently selected from the group consisting of hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino and di (C 1 -C 6 -alkyl) amino,
wherein R g is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 3 -C 8 -cycloalkyl,
wherein each aliphatic R 7 , R e , R f and R g may be substituted with one or more R 7Sa that may be the same or different,
wherein each cyclic or cyclic moiety of R 7 , each cyclic R e and each cyclic R g may be substituted with one or more R 7Se that may be the same or different,
R 7Sa is selected from the group consisting of cyano, hydroxyl, carboxyl, 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 , —Si(C 1 -C 6 -alkyl) 3 , aromatic C 6 -C 14 -carbocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
R 7Sc is selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, 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 non-aromatic 3- to 7-membered monocyclic heterocycle, or two R 7Se form, together with the carbon atom to which they are attached to, a C 3 -C 8 -cycloalkyl;

R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, aromatic C 6 -C 14 -carbocycle, non-aromatic 3- to 14-membered heterocycle, aromatic 5- to 14-membered heterocycle, C 3 -C 8 -cycloalkyloxy, aromatic C 6 -C 14 -carbocyclyloxy, non-aromatic 3- to 14-membered heterocyclyloxy, aromatic 5- to 14-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(Rh) 2 , —SR i , —S(═O)R i and —S(═O) 2 R i ,
wherein R h is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, aromatic C 6 -C 14 -carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein R i is selected from the group consisting of C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, aromatic C 6 -C 14 -carbocycle, aromatic 5- to 14-membered heterocycle and non-aromatic 3- to 7-membered monocyclic heterocycle,
wherein each aliphatic R 8 , R h and R i may be substituted with one or more R 8Sa that may be the same or different,

Assignees

• Bayer Ag
• Bayer Cropscience Ag

Inventors

• Chen Victor
• Cristau Pierre
• Dufour Jérémy
• Es-Sayed Mazen
• Geist Julie
• Gourgues Mathieu
• Loque Dominique
• Millet Anthony
• Rackl Daniel
• Rebstock Anne-Sophie
• Rinolfi Philippe
• Sato Yoshitaka
• Sudau Alexander
• Thomas Vincent
• Toquin Valérie

Classifications

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D405/12

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

• C07D401/12

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

• C07D401/04

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

• C07D237/24 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title