Antimicrobial compounds and their use in treating plant disease

Patent metadata

Field	Value
Publication number	US-9247749-B2
Application number	US-201414498454-A
Country	US
Kind code	B2
Filing date	Sep 26, 2014
Priority date	Mar 26, 2012
Publication date	Feb 2, 2016
Grant date	Feb 2, 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 in a citrus plant comprising administering to a citrus 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 plant disease is caused by Candidatus liberibacter asiaticus.

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

6. 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).

7. 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).

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

9. 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).

10. 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).

11. An agricultural composition, formulated to be administered to a plant, wherein said composition comprises 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); and a carrier; wherein the amount of the SecA inhibiting compound is effective in treating or preventing plant disease in a citrus plant.

12. The agricultural composition of claim 11 , further comprising an antimicrobial.

13. The agricultural composition of claim 11 , further comprising a plant fertilizer.

14. The composition, according to claim 11 , wherein said compound is N-(5-ethyl-1,3,4-thiadiazol-2-yl)-1-methyl-9H-beta-carboline-3-carboxamide (C16).

15. The composition, according to claim 11 , wherein said compound is 3-amino-6-phenyl-4-(3,4,5-trimethoxyphenyl)thieno[2,3-b]pyridine-2-carboxylic acid (C17).

16. The composition, according to claim 11 , wherein said compound is N-(1-{[(4-methoxyphenyl)amino]carbonyl}cyclohexyl)-4-(1H-tetrazol-1-yl)benzamide (C18).

17. The composition, according to claim 11 , wherein said compound is N-(6-methoxy-1,3-benzothiazol-2-yl)-2-[(5-methyl-1H-benzimidazol-2-yl)thio]acetamide (C19).

18. The composition, according to claim 11 , 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).

19. A method of treating or preventing plant disease in a citrus plant comprising administering to a citrus 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]diaze-pin-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).

20. The method of claim 19 , 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.

21. The method of claim 20 , wherein the composition is administered to the plant by injecting the composition into plant vasculature or by application to a root system.

22. The method of claim 19 , wherein the plant disease is caused by Candidalus liberibacter asiaticus.

23. The method of claim 19 , wherein the concentration of the SecA inhibiting compound in the composition is between about 100 μM and 1 mM.

24. The method, according to claim 19 , wherein said compound is N-(4-methoxyphenyl)-N-{1-[(4-methoxyphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC8).

25. The method, according to claim 19 , wherein said compound is 3-Amino-4-(4-fluorophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylic acid (SA2).

26. The method, according to claim 19 , wherein said compound is N-[(2S)-3-Methyl-1-oxo-1-{[3-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA3).

27. The method, according to claim 19 , 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).

28. The method, according to claim 19 , 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).

29. The method, according to claim 19 , 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).

30. The method, according to claim 19 , 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).

31. The method, according to claim 19 , 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).

32. The method, according to claim 19 , wherein said compound is 11-(4-hydroxy-3,5-dime

Assignees

• Univ Florida
• 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

• A01N43/78

  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

• A01N43/62

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

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title