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MolPort-001-812-996
Also known as: 85-00-7, Aquacide, Reglon, Reglox, Deiquat, Preeglone
Molecular Formula
C12H12Br2N2
Molecular Weight
344.04  g/mol
InChI Key
ODPOAESBSUKMHD-UHFFFAOYSA-L
FDA UNII
6BDV3T272W

A contact herbicide used also to produce desiccation and defoliation. (From Merck Index, 11th ed)
1 2D Structure

MolPort-001-812-996

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
7,10-diazoniatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene;dibromide
2.1.2 InChI
InChI=1S/C12H12N2.2BrH/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1;;/h1-8H,9-10H2;2*1H/q+2;;/p-2
2.1.3 InChI Key
ODPOAESBSUKMHD-UHFFFAOYSA-L
2.1.4 Canonical SMILES
C1C[N+]2=CC=CC=C2C3=CC=CC=[N+]31.[Br-].[Br-]
2.2 Other Identifiers
2.2.1 UNII
6BDV3T272W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dibromide, Diquat

2. Diquat

2.3.2 Depositor-Supplied Synonyms

1. 85-00-7

2. Aquacide

3. Reglon

4. Reglox

5. Deiquat

6. Preeglone

7. Reglone

8. Weedtrine-d

9. Diquat Dibromide [iso]

10. Ethylene Dipyridylium Dibromide

11. 6bdv3t272w

12. Detrone

13. 6,7-dihydrodipyrido[1,2-a:2',1'-c]pyrazine-5,8-diium Bromide

14. Ortho-diquat

15. Dipyrido(1,2-a:2',1'-c)pyrazinediium, 6,7-dihydro-, Dibromide

16. Caswell No. 402

17. Reglon Dibromide (ussr)

18. Deiquat Dibromide (ussr)

19. Diquat Dibromide 100 Microg/ml In Water

20. Hsdb 1700

21. Nsc-116553

22. Einecs 201-579-4

23. Pp 100

24. Epa Pesticide Chemical Code 032201

25. Nsc 116553

26. Unii-6bdv3t272w

27. 6,7-dihydrodipyrido[1,2-b:1',2'-e]pyrazine-5,8-diium;dibromide

28. 1,1'-ethylene 2,2'-dipyridylium Dibromide

29. 1,1'-ethylene-2,2'-bipyridinium Dibromide

30. 1,1'-ethylene-2,2'-bipyridylium Dibromide

31. 1,1'-ethylene-2,2'-dipyridylium Dibromide

32. 9,10-dihydro-8a,10a-diazoniaphenanthrene Dibromide

33. 1,1'-aethylen-2,2'-bipyridinium-dibromid [german]

34. 6,7-dihydrodipyrido(1,2-a:2',1'-c)pyrazinedium Dibromide

35. 1,1'-aethylen-2,2'-bipyridinium-dibromid

36. 9,10-dihydro-8a,10a-diazoniaphenanthrene(1,1'-ethylene-2,2'-bipyridylium)dibromide

37. Schembl52886

38. Diquat Dibromide [mi]

39. Diquat Dibromide [hsdb]

40. Chembl1599022

41. Dtxsid3024075

42. Diquat Dibromide [mart.]

43. Dipyrido(1,2-a;2',1'-c)pyrazinediium, 6,7-dihydro-, Dibromide

44. Mfcd00078635

45. Akos015902672

46. Dipyrido(1,2-a:2',1'-c)pyrazinediium, 6,7-dihydro-, Labeled With Carbon-14, Dibromide

47. Ncgc00163714-01

48. 34417-68-0

49. As-15492

50. Diquat Dibromide 100 Microg/ml In Methanol

51. Hy-122984

52. Cs-0090817

53. Ft-0729120

54. A917748

55. Q910903

56. 9,10-dihydro-8a,10a-diazophenanthrene Dibromide

57. 6,7-dihydrodipyrido[1,2-a:2',1'-c]pyrazinediium Dibromide

58. 6,7-dihydro-dipyrido(1,2-a:2',1-c)pyrazinediium Dibromide

59. 7,10-diazoniatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene;dibromide

60. Dipyrido(1,2-a:2',1'-c)pyrazinediium, 6,7-dihydro-, Bromide (1:2)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 344.04 g/mol
Molecular Formula C12H12Br2N2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass343.93467 g/mol
Monoisotopic Mass341.93672 g/mol
Topological Polar Surface Area7.8 Ų
Heavy Atom Count16
Formal Charge0
Complexity183
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)


Defoliants, Chemical

Herbicides that remove leaves from trees and growing plants. They may be either organic or inorganic. Several of the more persistent types have been used in military operations and many are toxic. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Defoliants, Chemical.)


4.2 Absorption, Distribution and Excretion

... (14)C-DIQUAT ... POORLY ABSORBED AFTER ORAL ADMIN TO RATS, AS WOULD BE EXPECTED FOR /CATION/. A RAT DOSED WITH (14)C-DIQUAT HAD EXCRETED 90% OF THE (14)C IN FECES & 6% IN URINE AFTER 48 HR ...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 85


... DIQUAT, PARAQUAT ... WERE STUDIED IN BILE-DUCT-CANNULATED RATS, GUINEA-PIGS & RABBITS. ... EXCRETED UNCHANGED IN BILE & URINE, EXCEPT DIQUAT, WHERE 18% OF DOSE WAS METABOLIZED BY THE RABBIT. ALL THE CATIONS WERE POORLY EXCRETED IN THE BILE (LESS THAN 10%).

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 575


... Diquat was applied in doses of 0, 0.2, 0.5, 0.75, & 1.0 ug/ml diquat cation. The concn of diquat initially followed an exponential decline; after day 3 the decline in concn in the 3 highest treatments was less precipitous. By day 5, diquat was below the min detectable level of 0.05 ug/ml in all treatments. Half-lives were as follows: 0.59, 0.79, & 0.88 days for treatments of 0.5, 0.75, & 1.0 ug/ml, respectively. Max concns of diquat in plant tissue rose to a peak on day 4 or 5, then gradually declined. Max mean tissue concns were 490 ug/g on day 5 (0.5 ug/ml treatment), 688 ug/g on day 5 (0.75 ug/ml treatment), & 869 ug/g on day 4 (1.0 ug/ml treatment). The lethal concn of diquat in hydrilla tissue was about 600 ug/g dry weight. Dissolved oxygen concns decreased until day 4 or 5, leveled off, & then rose after day 7. Expressed as a % of the control dissolved oxygen concn, treatment concns leveled off at about 80%, 40%, & 30% in the 0.2, 0.5, & 0.75-1.0 ug/ml treatments, respectively. Membrane permeability, expressed as incr in conductivity of deionized water over a 4 hr interval/gram (dry weight) of hydrilla tissue increased until day 4, plateaued until day 9, then declined. Chlorophyll A concns showed no statistically significant differences.

Cassidy K, Rodgers JH; Environ Toxicol Chem 8 (2): 133-40 (1989)


DIQUAT ... POORLY ABSORBED FROM THE GUT OF ANIMALS FOLLOWING ORAL ADMIN. ... DEMONSTRATED THAT ... LOWER QUANTITIES ... WERE ABSORBED FROM GUT OF COWS; ONLY 0.4-2.6% OF INGESTED DIQUAT & 0.26% OF ... PARAQUAT APPEARED IN THE URINE AND 0.015% OR LESS OF THE HERBICIDES (OR THEIR METABOLITES) APPEARED IN MILK.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 523


For more Absorption, Distribution and Excretion (Complete) data for DIQUAT DIBROMIDE (14 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

... AFTER ORAL ADMIN ... TO RATS, 77% OF DOSE APPEARED IN FECES AS DIQUAT, & 12% AS METABOLIC PRODUCTS, ALMOST HALF OF WHICH WAS MONOPYRIDONE OF DIQUAT.

Kearney, P.C., and D. D. Kaufman (eds.) Herbicides: Chemistry, Degredation and Mode of Action. Volumes 1 and 2. 2nd ed. New York: Marcel Dekker, Inc., 1975., p. 524


METABOLIC BREAKDOWN DOES NOT OCCUR IN PLANTS.

Weed Science Society of America. Herbicide Handbook. 4th ed. Champaign, IL: Weed Science Society of America, 1979. of America, 1979., p. 186


DIQUAT UNDERWENT PHOTOCHEMICAL DEGRADATION ... AFTER APPLICATION TO PLANTS. USING (14)C-RING- OR -ETHYLENE BRIDGE-LABELED DIQUAT, ONE MAJOR METABOLITE & SEVERAL MINOR CMPD ... OBSERVED ... THAT THE MAJOR METABOLITE WAS RADIOACTIVE IN BOTH INSTANCES INDICATED AT LEAST ONE INTACT RING. ... CMPD WAS /SHOWN/ ... TO BE TETRAHYDRO-OXO-PYRIDO-PYRAZINE.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 179


Free radicals were shown to be produced from paraquat and diquat incubated in the presence of reduced NADP and liver microsomes.

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. V4 391-392


For more Metabolism/Metabolites (Complete) data for DIQUAT DIBROMIDE (6 total), please visit the HSDB record page.


4.4 Biological Half-Life

... Diquat was applied in doses of 0, 0.2, 0.5, 0.75, & 1.0 ug/ml diquat cation. ... Half-lives were as follows: 0.59, 0.79, & 0.88 days for treatments of 0.5, 0.75, & 1.0 ug/ml, respectively. ... /Diquat/

Cassidy K, Rodgers JH; Environ Toxicol Chem 8 (2): 133-40 (1989)


...After intravascular admin of 1 mg/kg, toxicokinetic analysis of the plasma concn-time profile of diquat using a two-compartment model provided... /an/ elimination half life (t1/2) = 35.8: 8.9 hr.

Schultz IR et al; Aquatic Toxicology 33 (3-4): 297-310 (1995)


4.5 Mechanism of Action

Diquat was not significantly more potent than paraquat. Both produced dose- and time-dependent inhibition of DNA synthesis. /Diquat/

PMID:7245208 Carmines EL et al; Toxicol Appl Pharmacol 58 (3): 353-62 (1981)


Diquat ruptured mitochondria of type A of type II alveolar cells, which became necrotic. /Diquat/

HIRA K, TAKAMATSU H; KANKYO KAGAKU SOGO KENKYUSHO NENPO 6: 9-18 (1979)


...Diquat, a potent redox cycler that generates reactive oxygen species, has been used to study oxidative stress ... . Diquat reduces cell growth in /human/ neuroblastoma /SH-SY5Y/ cells and induces an adaptive antioxidant response, which are concn dependent and occur at sublethal concns. At higher concns, diquat alters mitochondrial function and becomes increasingly toxic.

Slaughter MR, Thakkar H et al; Toxicol Appl Pharmacol 178(2): p.63-70 (2002)


...The age-associated enhancement of diquat toxicity /in Fischer 344 rats/ could be due to an increased availability of iron for reaction with diquat-generated hydrogen peroxide and for stimulation of lipid and protein oxidation.

PMID:8382845 Rikans LE et al; Toxicol Appl Pharmacol 118 (2): 263-70 (1993)


For more Mechanism of Action (Complete) data for DIQUAT DIBROMIDE (6 total), please visit the HSDB record page.


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