Anthraquinones as inhibitors of sulfide production from sulfate-reducing bacteria

• US 5,385,842 A
• Filed: 08/13/1993
• Issued: 01/31/1995
• Est. Priority Date: 04/18/1990
• Status: Expired due to Term

• Current Assignee: Arkion Life Sciences
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Weimer, Paul J., Cooling, Frederick B. III, Odom, James M., Anderson, Albert G.
• Primary Examiner(s): Wityshyn, Michael G.
• Assistant Examiner(s): REARDON, TIMOTHY
• Application Number:
  US08/107,439
• Time in Patent Office: 536 Days
• Field of Search: 435/184, 435/262, 435/32, 435/262.5, 435/281, 435/800, 435/243, 435/266, 210/601, 210/764, 208/47
• US Class Current: 435/262
• CPC Class Codes: A01N 35/06 containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
• CPC Class Codes: C12Q 1/025 for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics antimicrobial activity C12Q1/18
• CPC Class Codes: C12Q 1/04 Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor C12Q1/6897 takes precedence
• CPC Class Codes: C12Q 2304/26 Quinone; Quinol

Abstract

A process for inhibiting sulfide production by sulfate-reducing bacteria by contacting certain anthraquinones with the medium containing the sulfate-reducing bacteria is disclosed, as well as an automated screening test for such inhibition.

Claims

1. A process for inhibiting sulfide production by sulfate-reducing bacteria comprising contacting a medium containing the sulfate-reducing bacteria with one or more of the following compounds under conditions and in an amount sufficient to inhibit sulfide production:

N-[1-(9,10-dihydro-9,10-dioxo)anthracenyl]-N'"'"'-(1-methylethyl)imidodicarbonimidic diamide hydrochloride;

1-Aminoanthraquinone;

2-Aminoanthraquinone;

1-Amino-4-hydroxyanthraquinone;

1,2-Diaminoanthraquinone;

2,6-Dihydroxyanthraquinone;

Anthraquinone-2-carboxylic acid;

1,5-Dihydroxyanthraquinone;

1,2-Dihydroxyanthraquinone;

2,2'"'"'-[(9,10-Dihydro-9,10-dioxo-1,5-anthracenediyl)-diimino]bis[5-methylbenzenesulfonic acid], di Na salt;

1,2,5,8-Tetrahydroxyanthraquinone;

4-Amino-9,10-dihydro-1,3-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid, monosodium salt;

1,8-Dihydroxyanthraquinone;

2,2'"'"'-[(9,10-Dihydro-9,10-dioxo-1,4-anthracenediyl)-diimino]bis[5-methylbenzenesulfonic acid], di Na salt;

1-Amino-2,4-dibromoanthraquinone;

5-Chloro-1-anthraquinonylamine;

2-Ethylanthraquinone;

1-Hydroxyanthraquinone;

2-(Hydroxymethyl)anthraquinone;

1-Amino-4-methoxyanthraquinone;

1-Amino-6,7-dichloroanthraquinone;

Benz[a]anthracene-7,12-dione;

1,8-Dihydroxy-3-methylanthraquinone;

10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione hydrochloride;

9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid;

(8S-cis)-8-Acetyl-10[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride;

1,2,4-Trihydroxyanthraquinone;

1-Aminoanthraquinone diazonium salt;

2,2'"'"'-Dimethyl-[1,1'"'"'-bianthracene]-9,9'"'"',10,10'"'"'-tetrone;

3-(D-apio-beta-D-Furanosyloxy)-1,8-dihydroxy-6-methyl-9,10-anthracenedione;

2-Chloroanthraquinone;

1,5-Dichloroanthraquinone;

1,4,5,8-Tetrachloroanthraquinone;

1-Chloroanthraquinone;

6. -Trifluoromethylanthraquinone. 2. The process of claim 1 for inhibiting sulfide production by sulfate-reducing bacteria, wherein the medium is contacted with a mixture of at least two of said compounds.

7. The process of claim 1 wherein the compound is 1,8-dihydroxyanthraquinone.

8. The process of claim 1 wherein the compound is 1-chloroanthraquinone or 2-chloroanthraquinone.

9. The process of claim 1 wherein the compound is 3-chloro-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid.

10. The process of claim 1 wherein the compound is 2-bromoanthraquinone.

11. The process of claim 1 wherein the compound is 1-fluoroanthraquinone.

12. The process of claim 1 wherein the compound is 1-cyanoanthraquinone.

13. The process of claim 1 wherein the compound is 2-Trifluoromethylanthroquinone.

14. The process of claim 1 wherein the compound is anthraquinone.

15. The process of claim 1 wherein the sulfate-reducing bacterium is selected from the group consisting of Desulfovibrio desulfuricans, D. salexigens, D. vulgaris, D. multispirans, and D. gigas.

16. The process of claim 1 wherein the one or more compounds are dissolved or suspended in a solvent prior to contact with the medium wherein said solvent is selected from the group consisting of water, ethanol, acetone, methanol, dimethylsulfoxide, dimethylformamide, or tetrahydrofuran, and other water-miscible solvents.

17. The process of claim 1 wherein the one or more compounds are contacted with the medium at a concentration of at least about 0.1 ppm.

18. The process of claim 1 further comprising addition of a reducing agent to the medium containing the sulfate-reducing bacteria to enhance inhibition.

19. The process of claim 14 wherein the reducing agent is sodium sulfide and is present in the medium at a concentration of from about 2 to about 4 mM.

20. The process of claim 1 wherein said medium is sewage.

21. The process of claim 1 wherein sulfate production by the sulfate-reducing bacteria is reduced by the contacting of the medium with the one or more of said compounds.

23. The process of claim 18 wherein the anthraquinone is 9,10-anthraquinone.

24. The process of claim 19 wherein said medium is sewage.

25. The process of claim 19 in which the species of the sulfate-reducing bacteria is selected from the group consisting of Desulfovibrio desulfuricans, D. salexigens, D. vulgaris, D. multispirans, and D. gigas.

29. The medium of claim 24 in which the species of the sulfate-reducing bacteria is selected from the group consisting of Desulfovibrio desulfuricans, D. Salexigens, D. vulgaris, D. multispirans, and D. gigas.

2. 8-Dichloroanthraquinone;

2-Bromo-3-methylathraquinone;

2-(2,2,2-Trimethylpropionamido) anthraquinone;

2,6-Bis[2-(dimethylamino)ethoxy]-9,10-anthracenedione;

2-Methyl-1-nitroanthraquinone;

1-Amino-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid;

9,10-Dihydro-5-nitro-9,10-dioxo-1-anthracenesulfonic acid;

3-Chloro-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;

50/50 Mixture by weight of 1,5-Dihydrocyanthraquinone and 1,8-Dihydroxycyanthraquinone;

Anthraquinone;

1,8-Dihydroxy-3-(hydroxymethyl)-anthraquinone;

7,16-Dichloro-6,15-dihydro-5,9,14,18-anthrazinetetrone;

1,2,3,4,5,8-Hexahydroxyanthraquinone;

2,4,5,7-Tetrabromo-1,8-dihydroxy-9,10-anthracenedione;

1,2,7-Trihydroxyanthraquinone;

1,4,5-Trihydroxy-2-methyl-9,10-anthracenedione;

1,4,5,7-Tetrahydroxy-2-methyl-9,10-anthracenedione;

1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione;

1,4,5,8-Tetrahydroxy-2-methyl-9,10-anthracenedione;

3. 5,8-Trihydroxy-3-methyl-9,10-anthracenedione;

1-Hydroxy-2-[(6-O-β

-D-xylopyranosyl-β

-D-glycopyranosyl)oxy]-9,10-anthracenedione;

2-Phenoxy quinizarin-3,4'"'"'-disulfonic acid, di K salt;

(+,-)-1-Acetoxy-8-hydroxy-1,4,4a,9a-tetrahydroanthraquinone;

1-Amino-4-[4-[(dimethylamino)methyl]phenyl]amino-9,10-anthracenedione;

1,5-Bis(2-carboxyanilino)-9,10-anthracenedione;

1,8-Dihydroxy-9-anthranol;

1,2,10-Anthracenetriol;

1-Amino-4-bromo-2-methylanthranquinone;

1,4-Diaminoanthraquinone;

2,6-Diaminoanthraquinone;

1-Amino-4 [4-[[4-chloro-6-[2,3, or 4-sulfophenyl]amino]-1,3,5-triazin-2-yl]amino]-3-sulfophenyl]amino]-9,10-dihyro-9, 10-dioxo-2-anthracenesulfonic acid;

Anthraquinone-1,5-disulfonic acid, di Na salt hydrate;

Anthraquinone-2,6-disulfonic acid, di Na salt;

Anthraquinone-2-sulfonic acid, sodium salt monohydrate;

1,2-Bis[(4-sulfophenyl)amino]-4-hydroxyanthraquinone;

3-Aminomethylalizarin-N,N-diacetic acid;

1-Amino-4-[[3-(ethenylsulfonyl)phenyl]-9,10-dihydro-9,10-dioxo]-2-anthracene sulfonic acid, monosodium salt;

1-(Methylamino)anthraquinone;

2.

4. 2'"'"'-[(9,10-Dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracendiyl)diimino]bis[5-methylbenzenesulfonic acid], di Na salt;

2,2'"'"'-[(9, 10-Dihydro-9,10-dioxo-1,4-anthracenediyl)diimino]bis[5-butylbenzenesulfonic acid];

1,1'"'"'-Iminobis[4-amino]9,10-anthracenedione, sulfonated;

1-Amino-9,10-dihydro-9,10-dioxo-4-(phenylamino)-2-anthracenesulfonic acid, Na salt;

4-[[4-(Acetylamino)phenyl]amino]-1-amino-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid, Na salt;

1-Amino-9,10-dihydro-9,10-dioxo-4-[[3[[2-(sulfoxy)ethyl]sulfonyl]phenyl]amino]-2-anthracenesulfonic acid, disodium salt;

1-Amino-4-[3-[4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfophenyl]amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid;

1-(9,10-Dihydro-9,10-dioxo-1-anthracenyl)-1,2-hydrazinedisulfonic acid, di Na salt;

9,10-Dihydro-5,6-dihydroxy-9,10-dioxo-1-anthracenesulfonic acid;

N-(4-Chloro-9,10-dihydro-9,10-dioxo-1-anthracenyl)benzamide;

1-Amino-4-bromo-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid, Na salt;

1-Amino-9,10-dihydro-4[[(4-methylphenyl)sulfonyl]amino]-9,10-dioxo-2-anthracenesulfonic acid, Na salt;

9,10-Dihydro-9,10-dioxo-2,3-anthracenedicarboxylic acid;

1,1'"'"'-Iminobis(4-nitro-9,10-anthracenedione);

1-Amino-4-chloro-2-methylanthraquinone;

5. 3-dimethyl-1,4-dihydroxyanthraquinone;

6-Methyl-1,3,8-trihydroxyanthraquinone;

1,4-Bis(methylamino)-anthraquinone;

N-(4-Amino-9,10-dihydro-3-methoxy-9,10-dioxo-1-anthracenyl)-4-methylbenzenesulfonamide;

[1,1'"'"'-Bianthracene]-9,9'"'"'10,10'"'"'-tetrone;

6,7-Dichloro-1,4-dihydroxyanthraquinone;

2-[[9,10-Dihydro-4-(methylamino)-9,10-dioxo-1-anthracenyl]amino]-5-methyl-benzenesulfonic acid, monosodium salt;

2,8-Diphenyl-anthra[2,1-d;

6,5-d'"'"']bisthiazole-6,12-dione;

2-Methoxy-3-methyl-9,10-anthracenedione;

1,4-Bis[(1-methylethyl)amino]-9,10-anthracenedione;

1,4-Bis[(2,4,6-triethylphenyl)amino]-9,10-anthracenedione;

1-(2-Hydroxyethyl)amino-4-methylaminoanthraquinone;

1,4-Bis[(4-methylphenyl)amino]9,10-anthracenedione;

2-Amino-3-hydroxyanthraquinone;

1-(Bromothio)anthraquinone;

1,8-Bis(phenylmethoxy)-9,10-anthracenedione;

1-Amino-2-(2-aminoethylthio)-4-hydroxyanthraquinone;

1,4-Bis(pentylamino)-9,10-anthracenedione;

1-Amino-2-bromo-4-hydroxyanthraquinone;

2-Propionamidoanthraquinone;

1,4-Diamino-2,3-bis(2-phenoxyethoxy)anthraquinone;

N-(5-Chloro-9,10-dihydro-9,10-dioxo-1-anthracenyl)benzamide;

Anthraquinone-1-arsonic Acid;

N,N'"'"'-[Iminobis(9,10-dihydro-9,10-dioxo-4,1-anthracenediyl)]-bisbenzamide;

1,4,5,8-Tetraaminoanthraquinone;

2-Methylanthraquinone;

9,10-Dihydro-9,10-dioxo-2,7-anthracenedisulfonic acid, di Na salt;

1,2,3-trihydroxyanthraquinone;

9,10-Dihydro-1,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid;

2-Amino-3-chloroanthraquinone;

1-Anthraquinonesulfonic acid, Na salt;

2-tert-butylanthraquinone;

1,4-Dihydroxyanthraquinone;

1,5-Diamino-4,8-dihydroxyanthraquinone;

1-Hydroxy-4-[(4-methylphenyl)amino]-9,10-anthracenedione;

1,4-Dimethylanthraquinone;

1,1'"'"'-Iminobis-9,10-anthracenedione;

2-(Cyclopropylcarboxamido)anthraquinone;

1-Amino-2-methylanthraquinone;

2-[(9,10-Dihydro-4-hydroxy-9,10-dioxo-1-anthracenyl)amino]-5-methyl-benzenesulfonic acid, Na salt;

2,2'"'"'-[(9,10-Dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)diimino]bis[5-methyl]benzenesulfonic acid;

1,4-Bis(ethylamino)-9,10-anthracenedione;

1,4-Diamino-5-nitroanthraquinone;

N-Benzyl-9,10-dihydro-9,10-dioxo-2-anthracenesulfonamide;

2-Bromoanthraquinone;

1-Fluoroanthraquinone;

1-Cyanoanthraquinone and;

22. A process for inhibiting sulfide production by sulfate-reducing bacteria, the process comprising contacting an anaerobic medium containing the bacteria with an anthraquinone, the anthraquinone selected from the group consisting of 9,10-anthraquinone, 1,8-dihydroanthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 2-bromoanthraquinone, and 1-fluoroanthraquinone, so that the final concentration of anthraquinone is at least 0.1 ppm.

27. The medium of claim 22 in which the species of the sulfate-reducing bacteria is selected from the group consisting of Desulfovibrio desulfuricans, D. salexigens, D. vulgaris, D. multispirans, and D. gigas.

28. The medium of claim 22 in which the anthraquinone is 9,10-anthraquinone.

26. An aqueous anaerobic medium comprising sulfate-reducing bacteria and at least 0.1 ppm of an anthraquinone, the anthraquinone selected from the group consisting of 9,10-anthraquinone, 1,8-dihydroanthraquinone, 1-chloroanthraquinone, 2-chloroanthraquinone, 2-bromoanthraquinone, and 1-fluoroanthraquinone.