Antimicrobial compounds and their use in treating plant disease

Patent metadata

Field	Value
Publication number	US-9521850-B2
Application number	US-201514957645-A
Country	US
Kind code	B2
Filing date	Dec 3, 2015
Priority date	Mar 26, 2012
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

The subject invention is directed toward antimicrobial agents and methods of treating and preventing infection by pathogenic microorganisms and endophytic microorganisms in a plant through the use of SecA inhibitors.

First claim

We claim:

1. A method of treating or preventing plant disease comprising administering to a plant in need thereof a composition comprising an effective amount of a SecA inhibiting compound selected from the group consisting of: N-(5-ethyl-1,3,4-thiadiazol-2-yl)-1-methyl-9H-beta-carboline-3-carboxamide (C16); 3-amino-6-phenyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid (C17); N-(1-{[(4-methoxyphenyl)amino]carbonyl}cyclohexyl)-4-(1H-tetrazol-1-yl)benzamide (C18); N-(6-methoxy-1,3-benzothiazol-2-yl)-2-[(5-methyl-1H-benzimidazol-2-yl)thio]acetamide (C19); and 7-benzoyl-11-(2-thienyl)-2,3,4,5,10,11-hexahydro-1H-diabenzo[b,e][1,4]diazepin-1-one (C20).

2. The method of claim 1 , wherein the composition is administered to the plant by a method selected from the group consisting of dusting, sprinkling, spraying, brushing, dipping, smearing, impregnating, injection of the composition into plant vasculature, and application to a root system.

3. The method of claim 2 , wherein the composition is administered to the plant by injecting the composition into plant vasculature or by application to a root system.

4. The method of claim 1 , wherein the method is practiced in conjunction with application of a fertilizer.

5. The method of claim 1 , wherein the plant disease is caused by Candidatus liberibacter asiaticus.

6. The method of claim 1 , wherein the concentration of the SecA inhibiting compound in the composition is between about 100 μM and 1 mM.

7. The method, according to claim 1 , wherein said compound is N-(5-ethyl-1,3,4-thiadiazol-2-yl)-1-methyl-9H-beta-carboline-3-carboxamide (C16).

8. The method, according to claim 1 , wherein said compound is 3-amino-6-phenyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid (C17).

9. The method, according to claim 1 , wherein said compound is N-(1-{[(4-methoxyphenyl)amino]carbonyl}cyclohexyl)-4-(1H-tetrazol-1-yl)benzamide (C18).

10. The method, according to claim 1 , wherein said compound is N-(6-methoxy-1,3-benzothiazol-2-yl)-2-[(5-methyl-1H-benzimidazol-2-yl)thio]acetamide (C19).

11. The method, according to claim 1 , wherein said compound is 7-benzoyl-11-(2-thienyl)-2,3,4,5,10,11-hexahydro-1H-diabenzo[b,e][1,4]diazepin-1-one (C20).

12. A method of treating or preventing plant disease comprising administering to a plant in need thereof a composition comprising an effective amount of a SecA inhibiting compound selected from the group consisting of: N-(4-methoxyphenyl)-N-{1-[(4-methoxyphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC8); N-(4-methoxyphenyl)-N-{1-[(2-methylphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC11); 2,6-Difluoro-N-[(2S)-3-methyl-1-oxo-1-{[4-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA1); 3-Amino-4-(4-fluorophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylic acid (SA2); N-[(2S)-3-Methyl-1-oxo-1-{[3-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA3); (11S)-7-Benzoyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA4); 7-Benzoyl-11-(4-methoxyphenyl)-3-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA5); 7-Benzoyl-11-(4-hydroxyphenyl)-3-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA6); 7-Benzoyl-11-(4-ethoxyphenyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA7); 7-Benzoyl-3-phenyl-11-(2-thienyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA8); and 11-(4-hydroxy-3,5-dimethylphenyl)-3,3-dimethyl-7-(phenylcarbonyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA9).

13. The method of claim 12 , wherein the composition is administered to the plant by a method selected from the group consisting of dusting, sprinkling, spraying, brushing, dipping, smearing, impregnating, injection of the composition into plant vasculature, and application to a root system.

14. The method of claim 13 , wherein the composition is administered to the plant by injecting the composition into plant vasculature or by application to a root system.

15. The method of claim 12 , wherein the method is practiced in conjunction with application of a fertilizer.

16. The method of claim 12 , wherein the plant disease is caused by Candidatus liberibacter asiaticus.

17. The method of claim 12 , wherein the concentration of the SecA inhibiting compound in the composition is between about 100 μM and 1 mM.

18. The method, according to claim 12 , wherein said compound is N-(4-methoxyphenyl)-N-{1-[(4-methoxyphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC8).

19. The method, according to claim 12 , wherein said compound is N-(4-methoxyphenyl)-N-{1-[(2-methylphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC11).

20. The method, according to claim 12 , wherein said compound is 2,6-Difluoro-N-[(2S)-3-methyl-1-oxo-1-{[4-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA1).

21. The method, according to claim 12 , wherein said compound is 3-Amino-4-(4-fluorophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylic acid (SA2).

22. The method, according to claim 12 , wherein said compound is N-[(2S)-3-Methyl-1-oxo-1-{[3-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA3).

23. The method, according to claim 12 , wherein said compound is (11S)-7-Benzoyl-11-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA4).

24. The method, according to claim 12 , wherein said compound is 7-Benzoyl-11-(4-methoxyphenyl)-3-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA5).

25. The method, according to claim 12 , wherein said compound is 7-Benzoyl-11-(4-hydroxyphenyl)-3-phenyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA6).

26. The method, according to claim 12 , wherein said compound is 7-Benzoyl-11-(4-ethoxyphenyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][ 1 , 4 ]diazepin-1-one (SA7).

27. The method, according to claim 12 , wherein said compound is 7-Benzoyl-3-phenyl-11-(2-thienyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA8).

28. The method, according to claim 12 , wherein said compound is 11-(4-hydroxy-3,5-dimethylphenyl)-3,3-dimethyl-7-(phenylcarbonyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA9).

Assignees

• Univ Florida

Inventors

• Wang Nian
• Akula Nagaraju

Classifications

• C05G3/60

  Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants · CPC title

• A01N43/90 Primary

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

• A01N43/62

  three- or four-membered rings or rings with more than six members · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/48

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