Fungicidal halomethyl ketones, hydrates and enol ethers and their mixtures

Patent metadata

Field	Value
Publication number	US-2025089717-A1
Application number	US-202418804481-A
Country	US
Kind code	A1
Filing date	Aug 14, 2024
Priority date	Aug 16, 2023
Publication date	Mar 20, 2025
Grant date	—

Abstract

Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof,

wherein
G, Z, L, J, A and T are as defined in the disclosure; and (b) at least one additional fungicidal compound.

Also disclosed is a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of Formula 1, an N-oxide, or salt thereof (e.g., as a component in the aforesaid composition). Also disclosed is a composition comprising: (a) at least one compound selected from the compounds of Formula 1 described above, N-oxides, and salts thereof; and at least one invertebrate pest control compound or agent. Also disclosed are compounds of Formula 1 including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof.

First claim

What is claimed is:

1 . A fungicidal composition comprising:
(a) at least one compound selected from the compounds of Formula 1, N-oxides, and salts thereof:

wherein
T is selected from the group consisting of:

wherein the bond extending to the left is attached to A;
R 1 is CF 3 , CHF 2 or CCl 3 ;
W is O, S or NR 3 ;
R 3 is H, cyano, nitro, C(═O)OH, benzyl, C 1 -C 4 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, OR 3a or NR 3b R 3c ;
R 3a is H, benzyl, C 1 -C 4 alkyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 haloalkylcarbonyl;
R 3b is H, C 1 -C 4 alkyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 haloalkylcarbonyl;
R 3c is H or C 1 -C 4 alkyl; or
R 3b and R 3c are taken together to form a 4- to 6-membered fully saturated heterocyclic ring, each ring containing ring members, in addition to the connecting nitrogen atom, selected from carbon atoms and up to 2 heteroatoms independently selected from up to 2 O, up to 2 S and up to 2 N atoms, each ring optionally substituted with up to 2 methyl groups;
X is O, S or NR 4a ;
Y is O, S or NR 4b ;
R 4a and R 4b are each independently H, hydroxy or C 1 -C 4 alkyl;
R 2a and R 2b are each independently H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 15 trialkylsilyl or C 3 -C 15 halotrialkylsilyl; or
R 2a and R 2b are taken together with the atoms X and Y to which they are attached to form a 5- to 7-membered saturated ring containing ring members, in addition to the atoms X and Y, selected from carbon atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy on carbon atom ring members;
R 2c is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl or trifluoromethylsulfonyl, each optionally substituted with up 2 substituents independently selected from cyano, hydroxy, SC≡N and C 1 -C 2 alkoxy;
R 2d is H, cyano, halogen or C 1 -C 4 alkyl;
when T is T-1 or T-2, then A is A 1 -A 2 -CR 5a R 5b , wherein A 1 is connected to J, and CR 5a R 5b is connected to T;
when T is T-3, then A is A 1 -A 2 , wherein A 1 is connected to J, and A 2 is connected to T;
A 1 is CR 5a R 5b , N(R 6 ), O or S;
A 2 is a direct bond, CR 5a R 5b , N(R 6 ), O or S;
each R 5a and R 5b is independently H, cyano, hydroxy, halogen, C(═O)OCH 3 or C 1 -C 4 alkyl;
each R 6 is independently H, C(═O)H, cyano, C 1 -C 4 alkyl or C 2 -C 4 alkylcarbonyl;
J is selected from the group consisting of:

wherein the bond extending to the left is attached to L, and the bond extending to the right is attached to A;
each R 7 is independently F, Cl, I, Br, cyano, methyl, trifluoromethyl or methoxy;
q is 0, 1, 2, 3 or 4;
L is (CR 8a R 8b ) n ;
each R 8a and R 8b is independently H, halogen, cyano, hydroxy, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy or C 1 -C 3 haloalkoxy;
n is 0, 1, 2 or 3;
G is phenyl is substituted with 1 to 3 substituents independently selected from R 9 and optionally substituted with up to 3 substituents independently selected from R 10 ;
G is a 5- to 6-membered heteroaromatic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring is substituted with 1 to 3 substituents independently selected from R 9 and optionally substituted with up to 3 substituents independently selected from R 10 ;
G is a 3- to 7-membered nonaromatic ring or an 8- to 11-membered bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and optionally up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O) 2 , each ring is substituted with 1 to 3 substituents independently selected from R 9 and optionally substituted with up to 3 substituents independently selected from R 10 ;
each R 9 is independently —(CR 11a R 11b ) m R 9a , C(═O)NR 12a R 12b , C(R 12e )═NR 12f , C 2 -C 6 alkyl(thiocarbonyl) or C 2 -C 6 alkoxy(thiocarbonyl);
each m is independently 1, 2 or 3;
each R 9a is independently C(═O)NR 12e R 12g , OC(═O)NR 12c R 12d or ONR 12i R 12j ; or C 2 -C 8 alkylcarbonyloxy, C 3 -C 9 alkenylcarbonyloxy, C 3 -C 9 alkynylcarbonyloxy, C 4 -C 9 cycloalkylcarbonyloxy, C 2 -C 8 alkoxycarbonyloxy, C 4 -C 9 cycloalkylalkylcarbonyloxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C 4 -C 10 cycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 8 cyanoalkoxy, C 2 -C 8 alkylthioalkoxy, C 2 -C 8 alkylsulfinylalkoxy, C 2 -C 8 alkylsufonylalkoxy, C 2 -C 8 alkoxycarbonylalkoxy, C 3 -C 9 alkoxycarbonylcarbonyloxy, C 2 -C 8 alkylcarbonylthio, C 3 -C 9 alkenylcarbonylthio, C 3 -C 9 alkynylcarbonylthio, C 5 -C 9 cycloalkylcarbonylthio, C 2 -C 8 alkoxycarbonylthio, C 2 -C 8 alkylaminocarbonylthio, C 3 -C 9 dialkylaminocarbonylthio, C 5 -C 9 cycloalkylalkylcarbonylthio, C 2 -C 8 alkylcarbonylamino, C 3 -C 9 alkenylcarbonylamino, C 3 -C 9 alkynylcarbonylamino, C 5 -C 10 cycloalkylcarbonylamino, C 2 -C 8 alkoxycarbonylamino, C 2 -C 8 alkylaminocarbonylamino, C 3 -C 9 dialkylaminocarbonylamino, C 5 -C 10 cycloalkylalkylcarbonylamino, C 2 -C 8 alkenylthio, C 2 -C 8 alkynylthio, C 2 -C 8 alkylthioalkylthio, C 4 -C 10 cycloalkylalkylthio, C 2 -C 8 cyanoalkylthio, C 2 -C 8 alkoxyalkylthio, C 2 -C 8 alkylsulfinylalkylthio, C 2 -C 8 alkylsufonylalkylthio, C 3 -C 9 alkoxycarbonylalkylthio, C 3 -C 9 alkylaminocarbonylalkylthio, C 4 -C 10 dialkylaminocarbonylalkylthio, C 3 -C 6 alkenyloxycarbonyl, C 4 -C 10 cycloalkoxycarbonyl, C 5 -C 10 cycloalkylalkoxycarbonyl, C 3 -C 9 alkoxycarbonylcarbonyl, C 3 -C 8 trialkylsilylalkoxy or C 3 -C 15 halotrialkylsilylalkoxy, each optionally substituted with up to 4 substituents independently selected from R 13 ;
each R 10 is independently cyano, halogen, hydroxy, nitro, —SH, SF 5 , CH(═O), C(═O)OH, NR 14a R 14b , C(═O)NR 14a R 14b , C(═O)C(═O)NR 14a R 14b , C(═S)NR 14a R 14b , C(R 15 )═NR 16 , N═CR 17 NR 18a R 18b or —U—V-Q; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 7 cycloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylaminosulfinyl, C 2 -C 6 dialkylaminosulfinyl, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylsulfonylamino, C 2 -C 6 alkylcarbonyl, C 4 -C 7 cycloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, C 4 -C 7 cycloalkoxycarbonyl, C 3 -C 6 alkoxycarbonylcarbonyl, C 2 -C 6 alkylcarbonyloxy, C 4 -C 7 cycloalkylcarbonyloxy, C 2 -C 6 alkoxycarbonyloxy, C 4 -C 7 cycloalkoxycarbonyloxy, C 2 -C 6 alkylaminocarbonyloxy, C 4 -C 7 cycloalkylaminocarbonyloxy, C 2 -C 6 alkylcarbonylamino, C 4 -C 7 cycloalkylcarbonylamino, C 2 -C 6 alkoxycarbonylamino, C 4 -C 7 cycloalkoxycarbonylamino, C 2 -C 6 alkylaminocarbony

Assignees

• Fmc Corp

Inventors

• Wang Hengbin
• Mhora Terence Tariro

Classifications

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/36

  five-membered rings · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• A01N43/40

  six-membered rings · CPC title

• A01N43/647 Primary

  Triazoles; Hydrogenated triazoles · CPC title