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2D Structure
Also known as: 114311-32-9, Pulsar, Raptor, Imazamox [iso], 3-pyridinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl]-5-(methoxymethyl)-, Mfcd03427427
Molecular Formula
C15H19N3O4
Molecular Weight
305.33  g/mol
InChI Key
NUPJIGQFXCQJBK-UHFFFAOYSA-N
FDA UNII
UG6793ON5F

Imazamox is a member of the imidazolinone class of herbicides. It is registered for post-emergence control of broadleaf weeds and grass in alfalfa, edible legumes and soybeans. It is a systemic herbicide that moves throughout the plant tissue and prevents plants from producing an essential enzyme, acetolactate synthase (ALS), which is not found in animals. This enzyme is key for the biosynthesis of branched chain amino acids. Susceptible plants will stop growing soon after treatment, but plant death and decomposition will occur over several weeks.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-(methoxymethyl)-2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid
2.1.2 InChI
InChI=1S/C15H19N3O4/c1-8(2)15(3)14(21)17-12(18-15)11-10(13(19)20)5-9(6-16-11)7-22-4/h5-6,8H,7H2,1-4H3,(H,19,20)(H,17,18,21)
2.1.3 InChI Key
NUPJIGQFXCQJBK-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
UG6793ON5F
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 114311-32-9

2. Pulsar

3. Raptor

4. Imazamox [iso]

5. 3-pyridinecarboxylic Acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl]-5-(methoxymethyl)-

6. Mfcd03427427

7. 5-(methoxymethyl)-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic Acid

8. Ug6793on5f

9. Dtxsid3034664

10. Chebi:83742

11. 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-(methoxymethyl)-3-pyridinecarboxylic Acid

12. 2-(4-isopropyl-4-methyl-5-oxo-1h-imidazol-2-yl)-5-(methoxymethyl)pyridine-3-carboxylic Acid

13. 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1h-imidazol-2-yl)-5-(methoxymethyl)nicotinic Acid

14. 2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1h-imidazol-2-yl)-5-(methoxymethyl)nicotinic Acid

15. 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl]-5-(methoxymethyl)-3-pyridinecarboxylic Acid

16. 3-pyridinecarboxylic Acid, 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-5-(methoxymethyl)-

17. Raptor (herbicide)

18. (+-)-imazamox

19. Cl29926;(+/-)-imazamox

20. Hsdb 7013

21. Unii-ug6793on5f

22. Ac 299263

23. Cl 299263

24. Einecs Annex I Index 613-208-00-7

25. Imazamox (standard)

26. Imazamox 10 Microg/ml In Acetonitrile

27. Imazamox [mi]

28. Raptor [hsdb]

29. Sweeper 70dg

30. 5-methoxymethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic Acid

31. Cl29926;()-imazamox

32. Schembl18640

33. (+/-)-imazamox

34. Chembl1881028

35. Dtxcid1014664

36. Schembl22939437

37. Glxc-25871

38. Tox21_301007

39. Akos015895776

40. Akos040741871

41. Cs-5783

42. Hy-100427r

43. Ncgc00163955-01

44. Ncgc00163955-02

45. Ncgc00163955-03

46. Ncgc00254909-01

47. As-13848

48. Ac-299263

49. Cl-299263

50. Db-041210

51. Hy-100427

52. Cas-114311-32-9

53. Imazamox, Pestanal(r), Analytical Standard

54. Ns00000438

55. C18598

56. F21405

57. J-003080

58. Q17166948

59. 2-[4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-methoxymethylnicotinic Acid

60. 5-methoxymethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) Nicotinic Acid

61. 5-(methoxymethyl)-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1h-imidazol-2-yl]pyridine-3-carboxylic Acid

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 305.33 g/mol
Molecular Formula C15H19N3O4
XLogP30.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area101
Heavy Atom Count22
Formal Charge0
Complexity491
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.)


4.2 Absorption, Distribution and Excretion

Plant absorption: Absorption occurs through both the foliage and roots.

US EPA; Pesticide Fact Sheet. Imazamox. Conditional Registration. August 22, 2000. Washington, DC: USEPA, Off Prev Pest Tox Sub (7501C).


Rapidly excreted primarily in the urine following iv admin /to rats/, and in the urine and feces following oral admin, mainly as unchanged parent.

US EPA; Pesticide Fact Sheet. Imazamox. Conditional Registration. August 22, 2000. Washington, DC: USEPA, Off Prev Pest Tox Sub (7501C).


Forty-four Sprague Dawley rats (5/sex/group) were dosed with (14)C-/imazamox/ by a single intravenous (iv) dose at 10 mg/kg or a single oral gavage dose according to the following regiments: (1) 10 mg/kg body weight; (2) 14-day preconditioning with 10 mg/kg non-radiolabelled /imazamox/, followed by 10 mg/kg (14)C-/imazamox/; or (3) 1000 mg/kg body weight. The elimination patterns indicated that the radioactive residue were rapidly cleared from the body (ca. 95%) excreted in urine and recovered within 12 hours after dosing for all dose groups. Approximately, 74-75% of the radioactivity was absorbed via oral administration at 10 mg/kg dose and 74.4-74.5% excreted in urine and 18.7- 24.0% in feces. Much higher proportion of the dose was excreted in feces following oral dose (18.7- 24.0%) compared to iv injection (1.9-2.7%), most likely due to incomplete absorption. Three components accounted for ca. 99% of the total urinary radioactivity (98.2%, parent; 0.6%, 5- hydroxymethyl-nicotinic acid metabolite; and 0.4%, 5-carboxy-nicotinic acid metabolite) and ca. 89% of the extractable radioactivity in the feces (76.4%, parent; 9.6%, 5-hydroxymethyl-nicotinic acid metabolite; and 2.5%, 5-carboxy-nicotinic acid metabolite). The radioactive residues in the tissues were low (< 0.007%), and no (14)C-residues were detected in the expired air.

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data for Imazamox (October, 2000)


In rats, imazamox was rapidly absorbed, and the oral absorption was approximately 75% of the administered dose. Urine was the major route of excretion (>74%).

Joint FAO/WHO Meeting on Pesticide Residues; Pesticide Residues in Food-214, Part II p. 231 (2014)


4.3 Metabolism/Metabolites

Imazamox is a racemic mixture. No information on chiral conversion in the mammalian metabolism or toxicity of specific enantiomer is available. However, information available in the fate and behaviour and residues section indicated that chiral conversion does not occur and exposure would be only to the racemic mixture.

EFSA Journal 14 (4): 4432 (2016)


Forty-four Sprague Dawley rats (5/sex/group) were dosed with (14)C-/imazamox/ ...Three components accounted for ca. 99% of the total urinary radioactivity (98.2%, parent; 0.6%, 5- hydroxymethyl-nicotinic acid metabolite; and 0.4%, 5-carboxy-nicotinic acid metabolite) and ca. 89% of the extractable radioactivity in the feces (76.4%, parent; 9.6%, 5-hydroxymethyl-nicotinic acid metabolite; and 2.5%, 5-carboxy-nicotinic acid metabolite). The radioactive residues in the tissues were low (<0.007%), and no (14)C-residues were detected in the expired air.

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data for Imazamox (October, 2000)


(14)C-(15)N-labelled/unlabelled imazamox mix was incubated with dog, rabbit, rat, mouse or human liver microsomes in the presence of a nicotinamide adenine dinucleotide phosphate (NADPH)-generating system. With 90% recovered radioactivity and above, only the parent molecule was detected in all test systems by high-performance liquid chromatographic analysis in fresh samples after the incubation. Under the conditions of the study, imazamox was not metabolized by liver microsomes of dogs, rabbits, rats, mice or humans. No unique human metabolite was detected. Under the conditions of the study, the positive control, testosterone, was metabolized by the microsome samples originating from different species.

Joint FAO/WHO Meeting on Pesticide Residues; Pesticide Residues in Food-214, Part II p. 231 (2014)


In rats, imazamox was rapidly absorbed, and the oral absorption was approximately 75% of the administered dose. Urine was the major route of excretion (>74%). Most of the elimination occurred within the first 24 hours after dosing, as unchanged parent compound. Smaller amounts of the test substance were excreted through faeces (>19% in animals receiving 10 mg/kg bw and approximately 10-20% in animals receiving 1000 mg/kg bw). Only trace amounts of tissue residue were detected. Imazamox appears not to be metabolized. Trace levels of imazamox-related compounds detected in the urine and faeces were attributed to the presence of impurities in the dosing solution, not to rat metabolism.

Joint FAO/WHO Meeting on Pesticide Residues; Pesticide Residues in Food-214, Part II p. 231 (2014)