Imazamethabenz
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MedKoo CAT#: 581230

CAS#: 81405-85-8

Description: Imazamethabenz is also known as Imazamethabenz-methyl, it is is a herbicide. A post-emergence herbicide, usually used as the methyl ester, to control grasses and some dicotyledonous weeds. Also pesticide transformation product. Activity and selectivity are due to differential de-esterification to the active parent acid in target and crop species. Imazamethabenz-methyl is used on cereals and sunflowers, especially against wild oat.


Chemical Structure

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Imazamethabenz
CAS# 81405-85-8

Theoretical Analysis

MedKoo Cat#: 581230
Name: Imazamethabenz
CAS#: 81405-85-8
Chemical Formula: C32H40N4O6
Exact Mass:
Molecular Weight: 576.69
Elemental Analysis: C, 66.65; H, 6.99; N, 9.72; O, 16.65

Price and Availability

Size Price Availability Quantity
100.0mg USD 230.0 2 Weeks
250.0mg USD 400.0 2 Weeks
500.0mg USD 650.0 2 Weeks
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Synonym: Imazamethabenz; Imazamethabenz-methyl; Assert; HSDB 6675; Dagger;

IUPAC/Chemical Name: methyl 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoate compound with methyl 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-methylbenzoate (1:1)

InChi Key: WXUNXXKSYBUHMK-UHFFFAOYSA-N

InChi Code: InChI=1S/2C16H20N2O3/c1-9(2)16(4)15(20)17-13(18-16)12-8-10(3)6-7-11(12)14(19)21-5;1-9(2)16(4)15(20)17-13(18-16)11-7-6-10(3)8-12(11)14(19)21-5/h2*6-9H,1-5H3,(H,17,18,20)

SMILES Code: C1(=NC(C(=O)N1)(C(C)C)C)c1c(ccc(c1)C)C(=O)OC.C1(=NC(C(=O)N1)(C(C)C)C)c1c(cc(cc1)C)C(=O)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 576.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Christiansen A, Peterson A, Anderson SC, Lass R, Johnson M, Nienow AM. Analysis of the Photodegradation of the Imidazolinone Herbicides Imazamox, Imazapic, Imazaquin, and Imazamethabenz-methyl in Aqueous Solution. J Agric Food Chem. 2015 Dec 23;63(50):10768-77. doi: 10.1021/acs.jafc.5b04663. Epub 2015 Dec 9. PubMed PMID: 26616105.

2: Pinna MV, Pusino A. Influence of the isomerism on the sorption of imazamethabenz-methyl by soil. Chemosphere. 2013 Apr;91(3):265-8. doi: 10.1016/j.chemosphere.2012.11.023. Epub 2012 Dec 6. PubMed PMID: 23219405.

3: Cessna AJ, Elliott JA, Bailey J. Leaching of three imidazolinone herbicides during sprinkler irrigation. J Environ Qual. 2012 May-Jun;41(3):882-92. doi: 10.2134/jeq2011.0198. PubMed PMID: 22565269.

4: Pintado S, Montoya MR, Mellado JM. Protonation-dissociation reactions of imazamethabenz-methyl and imazamethabenz-Acid in relation to their soil sorption and abiotic degradation. J Agric Food Chem. 2009 Dec 9;57(23):11292-6. doi: 10.1021/jf902845h. PubMed PMID: 19904942.

5: Polo-Díez LM, Santos-Delgado MJ, Valencia-Cabrerizo Y, León-Barrios Y. Simultaneous enantiomeric determinations of acid and ester imidazolinone herbicides in a soil sample by two-dimensional direct chiral liquid chromatography. Talanta. 2015 Nov 1;144:375-81. doi: 10.1016/j.talanta.2015.06.062. Epub 2015 Jun 23. PubMed PMID: 26452836.

6: Newsome WH, Collins PG. Determination of imazamethabenz in cereal grain by enzyme-linked immunosorbent assay. Bull Environ Contam Toxicol. 1991 Aug;47(2):211-6. PubMed PMID: 1912697.

7: Brigante M, Emmelin C, Ferronato C, Greca MD, Previtera L, Paisse JO, Chovelon JM. Effect of positional isomerism on the abiotic degradation of pesticides: Case of m- and p-imazamethabenz-methyl. Chemosphere. 2007 Jun;68(3):464-71. Epub 2007 Feb 22. PubMed PMID: 17320147.

8: Laganà A, Fago G, Marino A. Simultaneous determination of imidazolinone herbicides from soil and natural waters using soil column extraction and off-line solid-phase extraction followed by liquid chromatography with UV detection or liquid chromatography/electrospray mass spectroscopy. Anal Chem. 1998 Jan 1;70(1):121-30. PubMed PMID: 9435470.

9: Tan S, Evans RR, Dahmer ML, Singh BK, Shaner DL. Imidazolinone-tolerant crops: history, current status and future. Pest Manag Sci. 2005 Mar;61(3):246-57. Review. PubMed PMID: 15627242.

10: Liu C, Mu C, Li Z, Xu L. Imazamethabenz inhibits human breast cancer cell proliferation, migration and invasion via combination with Pin1. Mol Med Rep. 2017 May;15(5):3210-3214. doi: 10.3892/mmr.2017.6399. Epub 2017 Mar 28. PubMed PMID: 28350086.

11: Hall LM, Devine MD. Cross-Resistance of a Chlorsulfuron-Resistant Biotype of Stellaria media to a Triazolopyrimidine Herbicide. Plant Physiol. 1990 Jul;93(3):962-6. PubMed PMID: 16667607; PubMed Central PMCID: PMC1062615.

12: Plaza G, Osuna MD, De Prado R. Cross resistance to ALS-inhibiting herbicides in Euphorbia heterophylla L. biotypes resistant to imazethapyr. Commun Agric Appl Biol Sci. 2003;68(4 Pt A):335-9. PubMed PMID: 15149128.

13: Chin TE, Wong RB, Pont JL, Karu AE. Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides. J Agric Food Chem. 2002 Jun 5;50(12):3380-9. PubMed PMID: 12033799.

14: Nejad H, Safarpour MM, Cavalier T, Picard G, Souza M, Krynitsky AJ, Chiu S, Miller P, Stout SJ. Capillary electrophoresis determinative and LC-MS confirmatory method for screening selected imidazolinone herbicides from soil. J Capillary Electrophor. 1998 Jan-Apr;5(1-2):81-7. PubMed PMID: 10327374.

15: Christopher JT, Powles SB, Holtum JA. Resistance to Acetolactate Synthase-Inhibiting Herbicides in Annual Ryegrass (Lolium rigidum) Involves at Least Two Mechanisms. Plant Physiol. 1992 Dec;100(4):1909-13. PubMed PMID: 16653216; PubMed Central PMCID: PMC1075883.

16: Casado C, Osuna MD, De Prado R. Evaluation of resistance in Amaranthus quitensis Kunth populations to imazethapyr and other imidazolinones. Commun Agric Appl Biol Sci. 2003;68(4 Pt A):323-9. PubMed PMID: 15149126.

17: Christopher JT, Powles SB, Liljegren DR, Holtum JA. Cross-Resistance to Herbicides in Annual Ryegrass (Lolium rigidum) : II. Chlorsulfuron Resistance Involves a Wheat-Like Detoxification System. Plant Physiol. 1991 Apr;95(4):1036-43. PubMed PMID: 16668088; PubMed Central PMCID: PMC1077648.

18: Burns EE, Keith BK, Refai MY, Bothner B, Dyer WE. Proteomic and biochemical assays of glutathione-related proteins in susceptible and multiple herbicide resistant Avena fatua L. Pestic Biochem Physiol. 2017 Aug;140:69-78. doi: 10.1016/j.pestbp.2017.06.007. Epub 2017 Jun 9. PubMed PMID: 28755697.