Fungicidal oxadiazoles

Patent metadata

Field	Value
Publication number	US-11708358-B2
Application number	US-201816603449-A
Country	US
Kind code	B2
Filing date	Apr 5, 2018
Priority date	Apr 6, 2017
Publication date	Jul 25, 2023
Grant date	Jul 25, 2023

Abstract

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R1, L and J are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A compound selected from Formula 1, tautomers, N-oxides, and salts thereof,

wherein
R 1 is

wherein the floating bond on R 1 is connected to L in Formula 1 through any available carbon or nitrogen atom of the depicted ring;
x is 0, 1 or 2;
L is (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;
J is

wherein the bond projecting to the left is bonded to L, and the bond projecting to the right is bonded to the oxadiazole ring in Formula 1;
each R 5a is independently H or R 5 ; provided that at most only two R 5a substituents are other than H;
each R 2 is independently halogen, cyano, —CH(═O), —C(═O)OH, —C(═O)NR 3a R 3b , —C(R 6 )═NR 7 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 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 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, C 4 -C 7 cycloalkoxycarbonyl, C 2 -C 6 alkylcarbonyloxy or C 2 -C 6 alkylcarbonylamino, each optionally substituted with up to 2 substituents independently selected from R 10 ;
each 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 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 3 -C 5 alkoxycarbonylalkyl;
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 3 -C 8 halocycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from cyano, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl and C 3 -C 15 trialkylsilyl;
each R 4a and R 4b is independently H, halogen, methyl or methoxy;
each R 5 is methoxy;
each R 6 is independently H or methyl;
each R 7 is independently C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy or C 2 -C 4 alkynyloxy, each optionally substituted with up to 1 substituent selected from cyano, hydroxy and —C(═O)OH;
each R 10 is independently halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkoxyalkoxy, 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 or —C(R 13 )═NOR 14 ;
each U is independently a direct bond, C(═O)O or C(═O)NR 17 , wherein the atom to the left is connected to R 1 , and the atom to the right is connected to V;
each V is independently a direct bond, C 1 -C 3 alkylene, C 2 -C 4 alkenylene or C 3 -C 4 alkynylene;
each Q is independently phenyl, each optionally substituted with up to 2 substituents independently selected from R 12 ; or pyridinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl, oxazolyl, isoxazolyl, thienyl, isoxazolinyl, piperidinyl, morpholinyl or piperazinyl, each ring optionally substituted with up to 2 substituents independently selected from R 12 ;
each R 12 is independently halogen, cyano, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;
each R 13 is independently H, halogen, methyl or methoxy;
each R 14 is independently H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkylcarbonyl or C 2 -C 4 alkoxycarbonyl;
each R 17 is independently H, cyano, methyl or halomethyl;
n is 1, 2, or 3;
provided that:
(a) when R 1 is 1H-pyrazol-1-yl substituted with 1-2 substituents selected from CH 3 and J is unsubstituted phenyl, then L is other than CH 2 CH 2 , CH 2 CHF or CH(CH 3 );
(b) the compound of Formula 1 is not

wherein:
each R 1a may be the same or different;
m is 0; or
m is 1; R 1a is at the 3-position and is Cl or —CH(═O); or
m is 1; R 1a is at the 4-position and is halogen, cyano, —CH(═O), OHC(═O), C 2 -C 5 alkoxycarbonyl, NH 2 C(═O), CH 3 NHC(═O), CH 3 CH 2 NHC(═O), cyclopropyl-CH 2 NHC(═O), (CH 32 NC(═O), (CH 3 CH 2 ) 2 NC(═O), CH 3 ONHC(═O), CH 3 OCH 2 CH 2 NHC(═O), C≡CCH 2 NHC(═O), CH 3 ON(CH 3 )C(═O), CH 3 ON═CH CH 3 CH 2 ON═CH, CH 3 CH 2 CH 2 ON═CH, (CH 3 ) 2 CHON═CH or C≡CCH 2 ON═CH; or
m is 2; R 1a is at the 3- and 4-positions and is cyano, CF 2 H, CH 3 OCH 2 , C 2 -C 3 alkoxycarbonyl, cyclopropyl, phenyl or 4-chlorophenyl; or
m is 2; R 1a is at the 3- and 5-positions and is cyano, CH 3 , —CH(═O), CF 2 H, cyclopropyl, C 2 -C 3 alkoxycarbonyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl or 4-methoxyphenyl; or
m is 2; R 1a is at the 4- and 5-positions and is CF 2 H, cyclopropyl, CH 3 OCH 2 or C 2 -C 3 alkoxycarbonyl;
(c) the compound of Formula 1 is not

ethyl 1-[1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;
ethyl 1-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;
ethyl 1-[2-fluoro-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-1H-pyrazole-4-carboxylate;
3-[4-[[(1-methyl-1H-pyrazol-3-yl)oxy]methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-[[(5-methyl-1H-pyrazol-3-yl)oxy]methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-[(2-fluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-[(2,6-difluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-(phenoxymethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-[(4-fluorophenoxy)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole;
3-[4-[(3,5-diethyl-1H-pyrazol-1-yl)methyl]phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole; and
3-[2-methoxy-4-(phenoxymethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

2. A compound of claim 1 wherein:
R 1 is U-1, U-2 or U-12;
L is (CR 4a R 4b ) n ;
J is J 63;
each R 2 is independently —C(═O)NR 3a R 3b , —C(R 6 )═NR 7 or —U—V-Q; or C 2 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl or C 3 -C 6 alkynyloxycarbonyl, each optionally substituted with up to 1 substituent selected from R 10 ;
each R 3a is independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl or C 3 -C 5 alkoxycarbonylalkyl;
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 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 2 -C 6 alkoxyalkyl or C 2 -C 6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from C 2 -C 4 alkylcarbonyl and C 2 -C 4 alkoxycarbonyl;
each R 4a and R 4b is independently H or methyl;
each R 6 is independently H;
each R 7 is independently C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy or C 2 -C 4 alkynyloxy;
each R 10 is independently halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 5 alko

Assignees

• Fmc Corp

Inventors

• Pasteris Robert James
• Chittaboina Srinivas
• Mcmahon Travis Chandler
• Kamireddy Balreddy
• Reddy Ravisekhara Pochimireddy

Classifications

• A01P3/00

  Fungicides · CPC title

• A01N43/82

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

• C07D417/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D271/06

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title