Antimicrobial compounds and their use in treating plant disease

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-dimethylphenyl)-3,3-dimethyl-7-(phenylcarbonyl)-2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-one (SA9).

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

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

35. 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-(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-fluoro-phenyl)-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); and a carrier; wherein the amount of the SecA inhibiting compound is effective in treating or preventing plant disease in a citrus plant.

36. The agricultural composition of claim 35 , further comprising an antimicrobial.

37. The agricultural composition of claim 35 , further comprising a plant fertilizer.

38. The composition, according to claim 35 , wherein said compound is N-(4-methoxyphenyl)-N-{1-[(4-methoxyphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC8).

39. The composition, according to claim 35 , wherein said compound is 3-Amino-4-(4-fluorophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylic acid (SA2).

40. The composition, according to claim 35 , wherein said compound is N-[(2S)-3-Methyl-1-oxo-1-{[3-(1H-tetrazol-1-yl)phenyl]amino}-2-butanyl]benzamide (SA3).

41. The composition, according to claim 35 , 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).

42. The composition, according to claim 35 , 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).

43. The composition, according to claim 35 , 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).

44. The composition, according to claim 35 , 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).

45. The composition, according to claim 35 , 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).

46. The composition, according to claim 35 , 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).

47. The composition, according to claim 35 , wherein said compound is N-(4-methoxyphenyl)-N-{1-[(2-methylphenyl)carbamoyl]cyclohexyl}-4-(1H-tetrazol-1-yl)benzamide (SSC11).

48. The composition, according to claim 35 , 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).