Use of aryl carbamates in agriculture and other plant-related areas

Patent metadata

Field	Value
Publication number	US-9439436-B2
Application number	US-201514813480-A
Country	US
Kind code	B2
Filing date	Jul 30, 2015
Priority date	Sep 1, 2010
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

Disclosure is provided for methods of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, including applying thereto a treatment effective amount of an aryl carbamate as described herein, or an agriculturally acceptable salt thereof. Methods of enhancing a microbicide (e.g., including a copper, antibiotic, bacteriophage, etc.) and/or plant defense activator are also provided, including applying an active compound as described herein. Compositions comprising an aryl carbamate compound as described herein in an agriculturally acceptable carrier are also provided, and in some embodiments the compositions further include a microbicide (e.g., including copper, antibiotic, bacteriophage, etc.) and/or a plant defense activator.

First claim

That which is claimed is:

1. A method of removing or inhibiting bacterial biofilm formation or bacterial infection in a plant or plant part thereof, comprising applying to said plant or plant part a treatment effective amount of a compound of Formula (I):

wherein:
R 1 is an aryl, an amine-substituted aryl, or a heteroaryl having at least one nitrogen atom;
n=0 to 10, saturated or unsaturated;
each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl; and
R 3 is alkyl, substituted cycloalkyl or unsubstituted cycloalkyl,
or an agriculturally acceptable salt thereof.

2. The method of claim 1 , wherein said plant is a fruit crop plant or a vegetable crop plant.

3. The method of claim 1 , wherein said plant is a turfgrass or ornamental plant.

4. The method of claim 1 , wherein said bacterial biofilm formation or bacterial infection is citrus canker.

5. The method of claim 1 , wherein said plant is a citrus tree.

6. The method of claim 1 , wherein R 1 is phenyl.

7. The method of claim 1 , wherein n=1 to 5.

8. The method of claim 1 , wherein R 3 is alkyl.

9. The method of claim 1 , wherein said compound is ethyl-N-(2-phenethyl) carbamate, or an agriculturally acceptable salt thereof.

10. A method of removing or inhibiting bacterial biofilm formation or bacterial infection in a plant or plant part thereof, comprising applying to said plant or plant part a treatment effective amount of a compound of Formula (I):

wherein:
R 1 is an aryl, an amine-substituted aryl, or a heteroaryl having at least one nitrogen atom;
n=0 to 10, saturated or unsaturated;
each occurrence of R x and R y is present or absent (depending upon chain saturation), and is each independently H or alkyl;
R 2 is selected from the group consisting of: H, alkyl, alkenyl and alkynyl; and
R 3 is alkyl, substituted cycloalkyl or unsubstituted cycloalkyl,
or an agriculturally acceptable salt thereof,
in combination with a microbicide.

11. The method of claim 10 , wherein said microbicide comprises copper.

12. The method of claim 10 , wherein said microbicide comprises copper hydroxide.

13. The method of claim 10 , wherein said microbicide is an antibiotic or a bacteriophage.

14. The method of claim 10 , wherein said applying step is carried out by applying said active compound and said microbicide simultaneously.

15. The method of claim 10 , wherein said applying step is carried out by applying said active compound and said microbicide sequentially.

16. The method of claim 10 , wherein R 1 is phenyl.

17. The method of claim 10 , wherein n=1 to 5.

18. The method of claim 10 , wherein R 3 is alkyl.

19. The method of claim 10 , wherein said compound is ethyl-N-(2-phenethyl) carbamate, or an agriculturally acceptable salt thereof.

20. The method of claim 1 , wherein said bacterial biofilm formation or bacterial infection is caused by a Xanthomonas species.

21. The method of claim 1 , wherein said bacterial biofilm formation or bacterial infection is citrus canker is caused by Xanthomonas axonopodis.

22. The method of claim 10 , wherein said bacterial biofilm formation or bacterial infection is caused by a Xanthomonas species.

23. The method of claim 10 , wherein said bacterial biofilm formation or bacterial infection is citrus canker caused by Xanthomonas axonopodis.

24. A method of removing or inhibiting citrus canker in a plant or plant part in need thereof, comprising applying to said plant or plant part a treatment effective amount of ethyl-N-(2-phenethyl) carbamate, or an agriculturally acceptable salt thereof.

25. The method of claim 24 , wherein the citrus canker is caused by Xanthomonas axonopodis.

26. The method of claim 24 , wherein said ethyl-N-(2-phenethyl) carbamate, or an agriculturally acceptable salt thereof, is applied in combination with a microbicide.

27. The method of claim 26 , wherein said microbicide comprises copper.

28. The method of claim 26 , wherein said microbicide is an antibiotic.

29. The method of claim 26 , wherein said microbicide is a bacteriophage.

Assignees

• Univ North Carolina State

Inventors

• Melander Christian
• Rogers Steven A

Classifications

• C07D213/40

  Acylated substituent nitrogen atom · CPC title

• C07D209/14

  Radicals substituted by nitrogen atoms, not forming part of a nitro radical · CPC title

• A01N47/12 Primary

  containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring · CPC title

• A01N59/20

  Copper · CPC title

• C07C2101/14

  Chemistry & Metallurgy · mapped topic