3,5-disubstituted-4,5-dihydro-1,2,4-oxadiazoles and compositions and methods for controlling nematode pests

Patent metadata

Field	Value
Publication number	US-9232800-B2
Application number	US-201414180629-A
Country	US
Kind code	B2
Filing date	Feb 14, 2014
Priority date	Feb 15, 2013
Publication date	Jan 12, 2016
Grant date	Jan 12, 2016

Abstract

Provided herein are new 3,5-disubstituted-4,5-dihydro-1,2,4-oxadiazoles that exhibit nematicidal activity and are useful, for example, in compositions and methods for the control of unwanted nematodes.

First claim

What is claimed is:

1. A compound of Formula I, Formula II, or a salt thereof,

wherein A is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halogen, CF 3 , CH 3 , OCF 3 , OCH 3 , CN, and C(H)O; and
C is selected from the group consisting of thienyl, furanyl, isoxazolyl, pyrrolyl, and pyrrolidinyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen.

2. The compound of claim 1 wherein A is optionally independently substituted phenyl.

3. The compound of claim 1 wherein C is optionally independently substituted pyrrolyl.

4. The compound of claim 1 wherein C is optionally independently substituted thienyl.

5. The compound of claim 1 wherein C is optionally independently substituted furanyl.

6. The compound of claim 1 wherein the compound is of Formula Ia or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen; and
E is selected from the group consisting of O, S, and N—R 10 , wherein R 10 is alkyl.

7. The compound of claim 1 wherein the compound is of Formula Ib or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen; and
E is selected from the group consisting of O, S, and N—R 10 , wherein R 10 is alkyl.

8. The compound of claim 1 wherein the compound is of Formula Ic or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O; and
R 6 , R 7 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen.

9. The compound of claim 1 wherein the compound is of Formula IIa or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen; and
E is selected from the group consisting of O, S, and N—R 10 , wherein R 10 is alkyl.

10. The compound of claim 1 wherein the compound is of Formula IIb or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen; and
E is selected from the group consisting of O, S, and N—R 10 , wherein R 10 is alkyl.

11. The compound of claim 1 wherein the compound is of Formula IIc or a salt thereof,

wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O; and
R 6 , R 7 , R 8 and R 9 are selected from the group consisting of hydrogen, alkyl, alkoxy, cycloalkyl, haloalkyl, haloalkoxy, heterocyclyl, and halogen.

12. A compound of claim 1 wherein A is substituted phenyl and C is selected from the group consisting of optionally independently substituted pyrrolyl, thienyl, and furanyl.

13. A compound selected from the group consisting of:
3-phenyl-5-(thiophen-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
5-(furan-2-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-chlorophenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-fluorophenyl)-5-(thiophen-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-chlorophenyl)-5-(thiophen-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-bromophenyl)-5-(thiophen-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-bromophenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(2,4-dichlorophenyl)-5-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-bromophenyl)-5-(furan-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(2,4-difluorophenyl)-5-(thiophen-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-chlorophenyl)-5-(thiophen-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-chlorophenyl)-5-(furan-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-fluorophenyl)-5-(thiophen-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-fluorophenyl)-5-(furan-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(4-fluorophenyl)-5-(furan-3-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
5-phenyl-3-(1H-pyrrol-1-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
5-(3-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1,2,4-oxadiazole, or a salt thereof;
5-(4-chloro-2-methylp

Assignees

• Monsanto Technology Llc

Inventors

• Slomczynska Urszula J
• Haakenson William P

Classifications

• C07D271/06

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

• C07D409/04

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

• C07D407/04

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

• A01N43/82 Primary

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

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title