Compositions and methods for controlling nematodes

Patent metadata

Field	Value
Publication number	US-9426995-B2
Application number	US-201313763087-A
Country	US
Kind code	B2
Filing date	Feb 8, 2013
Priority date	Feb 10, 2009
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.

First claim

What is claimed is:

1. A coated seed wherein the coating comprises a compound of Formula VII or a salt thereof,

wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which may be optionally independently 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 2 -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 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, OCH 3 , OCF 3 , and C(H)O;
and
C is pyrrolyl, pyrrolyloxo, pyrrolythio, or pyrrolylalkyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of CH 3 , C 2 -C 10 alkyl, cycloalkyl, heterocycle, hydroxyalkyl, and halogen.

2. The coated seed of claim 1 comprising a compound of formula VIIa 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 7 , R g and R 9 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 10 alkyl, cycloalkyl, heterocycle, and halogen; and
X is a bond, CH 2 , O, or S.

3. The coated seed of claim 1 wherein the coating is applied to the seed as a composition comprising the compound in an aqueous carrier.

4. The coated seed of claim 3 wherein the composition comprises a surfactant.

5. The coated seed of claim 3 wherein the composition comprises a co-solvent.

6. The seed of claim 3 wherein the coating further comprises a pesticide.

7. The composition coated seed of claim 6 wherein the pesticide is selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.

8. A coated seed wherein the coating comprises a compound of Formula XII or a salt thereof,

wherein,
A is arylor arylalkyl, each of which may be optionally independently 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 2 -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 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O; and
C is selected from the group consisting of thienyl, furanyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH 3 , and OCF 3 ; and
X is CH 2 , O,or S.

9. The coated seed of claim 8 comprising a compound of Formula XIIa 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 g and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O, or S; and
X is CH 2 , O, or S.

10. The coated seed of claim 8 comprising a compound of Formula XIIb 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 g and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O, or S; and
X is CH 2 , O, or S.

11. The coated seed of claim 8 wherein the coating is applied to the seed as a composition comprising the compound in an aqueous carrier.

12. The coated seed of claim 11 wherein the composition comprises a surfactant.

13. The coated seed of claim 11 wherein the composition comprises a co-solvent.

14. The coated seed of claim 11 wherein the coating further comprises a pesticide.

15. The coated seed of claim 14 wherein the pesticide is selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.

Assignees

• Monsanto Technology Llc

Inventors

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

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A01N43/82 Primary

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

• C07D413/04 Primary

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

• C07D417/04

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

• C07D413/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title