Compositions and methods for controlling nematode pests

Patent metadata

Field	Value
Publication number	US-9907306-B2
Application number	US-201615099073-A
Country	US
Kind code	B2
Filing date	Apr 14, 2016
Priority date	Sep 2, 2010
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include certain 2,5-substituted tetrazoles.

First claim

What is claimed is:

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

wherein,
A is an optionally substituted aryl, wherein said substituents are selected from the group consisting of CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
and
C is a heteroaryl selected from the group consisting of 3-thienyl and 3-furanyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of F, Cl, Br, CH 3 , and OCF 3 ,
or C is selected from the group consisting of 1-pyrrolidinyl and pyrrolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, hydroxyalkyl, and halogen.

2. The compound of claim 1 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; and
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, and halogen.

3. The compound of claim 1 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;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl Br, CH 3 , and OCF 3 ; and
E is O or S.

4. The compound of claim 1 of Formula Id 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 through R 13 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, and halogen.

5. A compound of Formula II or a salt thereof,

wherein,
A is an optionally substituted aryl, wherein said substituents are selected from the group consisting of CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
and
C is a heteroaryl selected from the group consisting of thienyl and furanyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of F, Cl, Br, CH 3 and OCF 3 ,
or C is selected from the group consisting of pyrrolidinyl and pyrrolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, hydroxyalkyl and halogen.

6. The compound of claim 5 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; and
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, and halogen.

7. The compound of claim 5 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 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and OCF 3 ; and
E is O or S.

8. The compound of claim 5 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;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and OCF 3 ; and
E is O or S.

9. The compound of claim 5 of Formula IId 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 through R 13 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 4 alkyl, cycloalkyl, heterocycle, and halogen.

10. A nematicidal composition comprising a compound of claim 1 at a concentration sufficient to reduce the viability of a parasitic nematode.

11. The nematicidal composition of claim 10 wherein the composition comprises one or more of a surfactant, a co-solvent, a fungicide, an herbicide, or another pesticide.

12. A nematicidal composition comprising a compound of claim 5 at a concentration sufficient to reduce the viability of a parasitic nematode.

13. The nematicidal composition of claim 12 wherein the composition comprises one or more of a surfactant, a co-solvent, a fungicide, an herbicide, or another pesticide.

14. A treated seed comprising a nematicidal composition comprising a compound of Formula I or Formula II, or a salt thereof,

wherein,
A is selected from the group consisting of aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, and heteroarylthio, each of which may be optionally substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C

Assignees

• Monsanto Technology Llc

Inventors

• Slomczynska Urszula
• Dimmic Matt W
• Haakenson Jr William P
• Wideman Al
• Crawford Michael J

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A01C1/00

  Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting · CPC title

• C07D405/04

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

• C07D257/06 Primary

  with nitrogen atoms directly attached to the ring carbon atom · CPC title

• A01N43/64

  having rings with three nitrogen atoms as the only ring hetero atoms · CPC title