Fungicidal oxadiazoles and their mixtures

Patent metadata

Field	Value
Publication number	US-2024090503-A1
Application number	US-202118267619-A
Country	US
Kind code	A1
Filing date	Dec 16, 2021
Priority date	Dec 17, 2020
Publication date	Mar 21, 2024
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
R 1 , L and J 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.

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
R 1 is a phenyl ring optionally substituted with up to 3 substituents independently selected from R 2 ; or
R 1 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, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O) 2 , each ring optionally substituted with up to 3 substituents independently selected from R 2 ; or
R 1 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 or ring system optionally substituted with up to 3 substituents independently selected from R 2 ;
L is O, NR 3 , NR 3 CH 2 , CH 2 NR 3 , NR 3 CH 2 CH 2 , CH 2 CH 2 NR 3 , (CR 4a R 4b ) n , OCH 2 , CH 2 O, OCH 2 CH 2 , CH 2 CH 2 O or CH 2 OCH 2 , wherein the atom to the left is connected to R 1 , and the atom to the right is connected to J, each carbon atom is optionally substituted with up to 2 substituents independently selected from halogen, cyano, hydroxy, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 2 alkoxy and C 1 -C 2 haloalkoxy;
J is a phenyl ring or a naphthalenyl ring system, each optionally substituted with up to 2 substituents independently selected from R 5 ; or a 3- to 7-membered carbocyclic ring, wherein up to 3 ring members are independently selected from C(═O) and C(═S), each ring optionally substituted with up to 2 substituents independently selected from R 5 ; or
J is a 5- to 6-membered heterocyclic 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, wherein up to 2 ring members are independently selected from C(═O), C(═S), S(═O) and S(═O) 2 , each ring optionally substituted with up to 2 substituents independently selected from R 5 ;
each R 2 is independently halogen, cyano, hydroxy, nitro, thioyl, SF 5 , CH(═O), C(═O)OH, —NR 3a R 3b , C(═O)NR 3a R 3b , C(═O)C(═O)NR 3a R 3b , C(═S)NR 3a R 3b , C(R 6 )═NR 7 , N═CR 8 NR 9a R 9b 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 alkyloxycarbonylcarbonyl, 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 alkylaminocarbonylamino, C 4 -C 7 cycloalkylaminocarbonylamino or C 2 -C 6 dialkoxyphosphinyl, each optionally substituted with up to 3 substituents independently selected from R 10 ;
each R 3 and R 3a is independently H, cyano, hydroxy, 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, C 1 -C 5 alkoxy, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylthioalkyl, C 2 -C 4 alkylsulfinylalkyl, C 2 -C 4 alkylsulfonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 4 -C 7 cycloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 3 -C 5 alkoxycarbonylalkyl, C 2 -C 5 alkylaminocarbonyl or C 3 -C 5 dialkylaminocarbonyl;
each R 3b is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 8 alkoxyalkoxyalkyl, C 2 -C 6 alkylthioalkyl, C 2 -C 6 alkylsulfinylalkyl, C 2 -C 6 alkylsulfonylalkyl, C 2 -C 6 alkylaminoalkyl, C 2 -C 6 haloalkylaminoalkyl, C 3 -C 8 dialkylaminoalkyl or C 4 -C 10 cycloalkylaminoalkyl, each optionally substituted with up to 1 substituent selected from cyano, hydroxy, nitro, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 3 -C 15 trialkylsilyl and C 3 -C 15 halotrialkylsilyl; or
a pair of R 3a and R 3b substituents are taken together with the nitrogen atom to which they are attached 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 3 substituents independently selected from halogen and C 1 -C 3 alkyl;
each R 4a and R 4b is independently H, halogen, cyano, hydroxy, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy; or
a pair of R 4a and R 4b substituents attached to the same carbon atom are taken together to form a C 3 -C 5 cycloalkyl ring optionally substituted with up to 2 substituents independently selected from halogen, methyl, methoxy and methylthio;
each R 5 is independently hydroxy, cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl or C 1 -C 4 alkoxy;
each R 6 is independently H, cyano, halogen, methyl, methoxy, methylthio or methoxycarbonyl;
each R 7 is independently hydroxy or NR 11a R 11b ; or C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 5 alkoxycarbonyloxy, C 2 -C 5 alkylaminocarbonyloxy or C 3 -C 5 dialkylaminocarbonyloxy, each optionally substituted with up to 1 substituent selected from halogen, cyano, hydroxy and —C(═O)OH;
each R 8 is independently H, methyl, methoxy or methylthio;
each R 9a and R 9b is independently H or C 1 -C 4 alkyl; or
a pair of R 9a and R 9b substituents are taken together with the nitrogen atom to which they are attached to form a 5- 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;
each R 10 is independently halogen, amino, cyano, hydroxy, nitro, thioyl, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alkoxycarbonyl, C 1 -C 6 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 5 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 3 -C 5 alkylthioalkylcarbonyl, C 3 -C 15 trialkylsily, C 3 -C 15 halotrialkylsilyl, C(R 13 )═NOR 14 or C(R 15 )═NR

Assignees

• Fmc Corp

Inventors

• Pasteris Robert James
• Chittaboina Srinivas
• Mcmahon Travis Chandler
• Kamireddy Balreddy
• Reddy Ravisekhara P
• Vega-Jimenez Byron
• Uppalapati Srinivasa Rao

Classifications

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title

• A01N25/30

  characterised by the surfactants · CPC title

• A01P3/00

  Fungicides · CPC title

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title