US 11,708,358 B2
Fungicidal oxadiazoles
Robert James Pasteris, Newark, DE (US); Srinivas Chittaboina, Bibipet (IN); Travis Chandler McMahon, Middletown, DE (US); Balreddy Kamireddy, Hockessin, DE (US); and Ravisekhara Pochimireddy Reddy, Secunderabad (IN)
Assigned to FMC Corporation, Philadelphia, PA (US)
Appl. No. 16/603,449
Filed by FMC Corporation, Philadelphia, PA (US)
PCT Filed Apr. 5, 2018, PCT No. PCT/US2018/026232
§ 371(c)(1), (2) Date Oct. 7, 2019,
PCT Pub. No. WO2018/187553, PCT Pub. Date Oct. 11, 2018.
Claims priority of provisional application 62/542,949, filed on Aug. 9, 2017.
Claims priority of provisional application 62/482,343, filed on Apr. 6, 2017.
Prior Publication US 2020/0148672 A1, May 14, 2020
Int. Cl. C07D 271/06 (2006.01); C07D 413/10 (2006.01); C07D 413/04 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01); C07D 417/10 (2006.01); C07D 471/04 (2006.01); C07D 487/04 (2006.01); C07D 498/04 (2006.01); A01N 43/82 (2006.01); A01N 43/84 (2006.01)
CPC C07D 413/10 (2013.01) [A01N 43/82 (2013.01); A01N 43/84 (2013.01); C07D 271/06 (2013.01); C07D 413/04 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07D 417/10 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01); C07D 498/04 (2013.01)] 14 Claims
 
1. A compound selected from Formula 1, tautomers, N-oxides, and salts thereof,

OG Complex Work Unit Chemistry
wherein
R1 is

OG Complex Work Unit Chemistry
wherein the floating bond on R1 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 (CR4aR4b)n, OCH2, CH2O, OCH2CH2, CH2CH2O or CH2OCH2; wherein the atom to the left is connected to R1, and the atom to the right is connected to J;
J is

OG Complex Work Unit Chemistry
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 R5a is independently H or R5; provided that at most only two R5a substituents are other than H;
each R2 is independently halogen, cyano, —CH(═O), —C(═O)OH, —C(═O)NR3aR3b, —C(R6)═NR7 or —U—V-Q; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C7 cycloalkoxy, C1-C6 alkylthio, C2-C6 alkoxycarbonyl, C3-C6 alkenyloxycarbonyl, C3-C6 alkynyloxycarbonyl, C4-C7 cycloalkoxycarbonyl, C2-C6 alkylcarbonyloxy or C2-C6 alkylcarbonylamino, each optionally substituted with up to 2 substituents independently selected from R10;
each R3a is independently H, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl or C3-C5 alkoxycarbonylalkyl;
each R3b is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 halocycloalkyl, C4-C10 cycloalkylalkyl, C4-C10 halocycloalkylalkyl, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl, each optionally substituted with up to 1 substituent selected from cyano, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl and C3-C15 trialkylsilyl;
each R4a and R4b is independently H, halogen, methyl or methoxy;
each R5 is methoxy;
each R6 is independently H or methyl;
each R7 is independently C1-C4 alkoxy, C2-C4 alkenyloxy or C2-C4 alkynyloxy, each optionally substituted with up to 1 substituent selected from cyano, hydroxy and —C(═O)OH;
each R10 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkoxy, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkylcarbonyl, C2-C4 haloalkylcarbonyl, C2-C5 alkoxycarbonyl or —C(R13)═NOR14;
each U is independently a direct bond, C(═O)O or C(═O)NR17, wherein the atom to the left is connected to R1, and the atom to the right is connected to V;
each V is independently a direct bond, C1-C3 alkylene, C2-C4 alkenylene or C3-C4 alkynylene;
each Q is independently phenyl, each optionally substituted with up to 2 substituents independently selected from R12; 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 R12;
each R12 is independently halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl or C1-C2 alkoxy;
each R13 is independently H, halogen, methyl or methoxy;
each R14 is independently H, C1-C2 alkyl, C1-C2 haloalkyl, C2-C4 alkenyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
each R17 is independently H, cyano, methyl or halomethyl;
n is 1, 2, or 3;
provided that:
(a) when R1 is 1H-pyrazol-1-yl substituted with 1-2 substituents selected from CH3 and J is unsubstituted phenyl, then L is other than CH2CH2, CH2CHF or CH(CH3);
(b) the compound of Formula 1 is not

OG Complex Work Unit Chemistry
wherein:
each R1a may be the same or different;
m is 0; or
m is 1; R1a is at the 3-position and is Cl or —CH(═O); or
m is 1; R1a is at the 4-position and is halogen, cyano, —CH(═O), OHC(═O), C2-C5 alkoxycarbonyl, NH2C(═O), CH3NHC(═O), CH3CH2NHC(═O), cyclopropyl-CH2NHC(═O), (CH32NC(═O), (CH3CH2)2NC(═O), CH3ONHC(═O), CH3OCH2CH2NHC(═O), C≡CCH2NHC(═O), CH3ON(CH3)C(═O), CH3ON═CH CH3CH2ON═CH, CH3CH2CH2ON═CH, (CH3)2CHON═CH or C≡CCH2ON═CH; or
m is 2; R1a is at the 3- and 4-positions and is cyano, CF2H, CH3OCH2, C2-C3 alkoxycarbonyl, cyclopropyl, phenyl or 4-chlorophenyl; or
m is 2; R1a is at the 3- and 5-positions and is cyano, CH3, —CH(═O), CF2H, cyclopropyl, C2-C3 alkoxycarbonyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl or 4-methoxyphenyl; or
m is 2; R1a is at the 4- and 5-positions and is CF2H, cyclopropyl, CH3OCH2 or C2-C3 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.