Linuron | CAS#330-55-2 | Herbicide

MedKoo Cat#: 591299 | Name: Linuron

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Linuron is a phenylurea herbicide that is used to control the growth of grass and weeds for the purpose of supporting the growth of crops like soybeans.

Chemical Structure

Linuron

CAS#330-55-2

Theoretical Analysis

MedKoo Cat#: 591299

Name: Linuron

CAS#: 330-55-2

Chemical Formula: C9H10Cl2N2O2

Exact Mass: 248.0119

Molecular Weight: 249.09

Elemental Analysis: C, 43.40; H, 4.05; Cl, 28.46; N, 11.25; O, 12.85

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 250.00	2 Weeks

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Related CAS #

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Synonym

Linuron; Garnitan; Herbicide 326

IUPAC/Chemical Name

Urea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methyl-

InChi Key

XKJMBINCVNINCA-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H10Cl2N2O2/c1-13(15-2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)

SMILES Code

O=C(NC1=CC=C(Cl)C(Cl)=C1)N(OC)C

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Linuron is a photosystem II inhibitor. Linuron is also a competitive androgen receptor (AR) antagonist with a Ki of 100 μM.

In vitro activity:

Linuron inhibited dihydrotestosterone (DHT)-hAR induced gene expression in CV-1 and MDA-MB-453-KB2 cells (EC(50) = 10 microM) at concentrations that were not cytotoxic. Reference: Toxicol Sci. 2000 Aug;56(2):389-99. https://pubmed.ncbi.nlm.nih.gov/10910998/

In vivo activity:

This study used RNA-seq to characterize the hepatic transcriptional response of mature male brown trout exposed for 4 days to 1.7, 15.3, and 225.9 μg/L linuron. This study identified a striking decrease in the expression of transcripts encoding the majority of enzymes forming the cholesterol biosynthesis pathway. This study also measured a very significant decrease in total hepatic cholesterol in fish exposed to 225.9 μg/L linuron and a negative correlation between total cholesterol and linuron treatment concentration. This study hypothesizes that inhibition of cholesterol biosynthesis may result from the disruption of androgen signaling by linuron. Reference: Environ Sci Technol. 2015 Mar 3;49(5):3110-8. https://pubmed.ncbi.nlm.nih.gov/25633873/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	401.46

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 249.09 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.

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

Formulation protocol:

1. Wilson VS, Lambright CR, Furr JR, Howdeshell KL, Earl Gray L Jr. The herbicide linuron reduces testosterone production from the fetal rat testis during both in utero and in vitro exposures. Toxicol Lett. 2009 Apr 25;186(2):73-7. doi: 10.1016/j.toxlet.2008.12.017. Epub 2009 Jan 9. PMID: 19167474. 2. Lambright C, Ostby J, Bobseine K, Wilson V, Hotchkiss AK, Mann PC, Gray LE Jr. Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats. Toxicol Sci. 2000 Aug;56(2):389-99. doi: 10.1093/toxsci/56.2.389. PMID: 10910998. 3. Ding H, Zheng W, Han H, Hu X, Hu B, Wang F, Su L, Li H, Li Y. Reproductive toxicity of linuron following gestational exposure in rats and underlying mechanisms. Toxicol Lett. 2017 Jan 15;266:49-55. doi: 10.1016/j.toxlet.2016.12.013. Epub 2016 Dec 19. PMID: 28007637; PMCID: PMC5697898. 4. Uren Webster TM, Perry MH, Santos EM. The herbicide linuron inhibits cholesterol biosynthesis and induces cellular stress responses in brown trout. Environ Sci Technol. 2015 Mar 3;49(5):3110-8. doi: 10.1021/es505498u. Epub 2015 Feb 12. PMID: 25633873.

In vitro protocol:

In vivo protocol:

1. Ding H, Zheng W, Han H, Hu X, Hu B, Wang F, Su L, Li H, Li Y. Reproductive toxicity of linuron following gestational exposure in rats and underlying mechanisms. Toxicol Lett. 2017 Jan 15;266:49-55. doi: 10.1016/j.toxlet.2016.12.013. Epub 2016 Dec 19. PMID: 28007637; PMCID: PMC5697898. 2. Uren Webster TM, Perry MH, Santos EM. The herbicide linuron inhibits cholesterol biosynthesis and induces cellular stress responses in brown trout. Environ Sci Technol. 2015 Mar 3;49(5):3110-8. doi: 10.1021/es505498u. Epub 2015 Feb 12. PMID: 25633873.

1: Su M, Jia L, Wu X, Sun H. Residue investigation of some phenylureas and tebuthiuron herbicides in vegetables by ultra-performance liquid chromatography coupled with integrated selective accelerated solvent extraction-clean up in situ. J Sci Food Agric. 2018 Mar 24. doi: 10.1002/jsfa.9014. [Epub ahead of print] PubMed PMID: 29574757. 2: Azab E, Kebeish R, Hegazy AK. Expression of the human gene CYP1A2 enhances tolerance and detoxification of the phenylurea herbicide linuron in Arabidopsis thaliana plants and Escherichia coli. Environ Pollut. 2018 Jul;238:281-290. doi: 10.1016/j.envpol.2018.03.025. Epub 2018 Mar 22. PubMed PMID: 29573710. 3: Fu L, Lu X, Tan J, Wang L, Chen J. Multiresidue determination and potential risks of emerging pesticides in aquatic products from Northeast China by LC-MS/MS. J Environ Sci (China). 2018 Jan;63:116-125. doi: 10.1016/j.jes.2017.09.010. Epub 2017 Sep 29. PubMed PMID: 29406095. 4: Albers P, Weytjens B, De Mot R, Marchal K, Springael D. Molecular processes underlying synergistic linuron mineralization in a triple-species bacterial consortium biofilm revealed by differential transcriptomics. Microbiologyopen. 2018 Apr;7(2):e00559. doi: 10.1002/mbo3.559. Epub 2018 Jan 3. PubMed PMID: 29314727; PubMed Central PMCID: PMC5911999. 5: Quintaneiro C, Soares AMVM, Monteiro MS. Effects of the herbicides linuron and S-metolachlor on Perez's frog embryos. Chemosphere. 2018 Mar;194:595-601. doi: 10.1016/j.chemosphere.2017.11.171. Epub 2017 Nov 29. PubMed PMID: 29241134. 6: Souza LP, Faroni LRD, Heleno FF, Pinto FG, Queiroz MELR, Prates LHF. Ozone treatment for pesticide removal from carrots: Optimization by response surface methodology. Food Chem. 2018 Mar 15;243:435-441. doi: 10.1016/j.foodchem.2017.09.134. Epub 2017 Sep 30. PubMed PMID: 29146362. 7: Albers P, Lood C, Özturk B, Horemans B, Lavigne R, van Noort V, De Mot R, Marchal K, Sanchez-Rodriguez A, Springael D. Catabolic task division between two near-isogenic subpopulations co-existing in a herbicide-degrading bacterial consortium: consequences for the interspecies consortium metabolic model. Environ Microbiol. 2018 Jan;20(1):85-96. doi: 10.1111/1462-2920.13994. Epub 2017 Dec 15. PubMed PMID: 29124862. 8: Wrobel MH, Mlynarczuk J. The inhibition of myometrial contractions by chlorinated herbicides (atrazine and linuron), and their disruptive effect on the secretory functions of uterine and ovarian cells in cow, in vitro. Pestic Biochem Physiol. 2017 Oct;142:44-52. doi: 10.1016/j.pestbp.2017.01.002. Epub 2017 Jan 5. PubMed PMID: 29107246. 9: Fraser TWK, Khezri A, Lewandowska-Sabat AM, Henry T, Ropstad E. Endocrine disruptors affect larval zebrafish behavior: Testing potential mechanisms and comparisons of behavioral sensitivity to alternative biomarkers. Aquat Toxicol. 2017 Dec;193:128-135. doi: 10.1016/j.aquatox.2017.10.002. Epub 2017 Oct 6. PubMed PMID: 29078070. 10: Gandar A, Laffaille P, Canlet C, Tremblay-Franco M, Gautier R, Perrault A, Gress L, Mormède P, Tapie N, Budzinski H, Jean S. Adaptive response under multiple stress exposure in fish: From the molecular to individual level. Chemosphere. 2017 Dec;188:60-72. doi: 10.1016/j.chemosphere.2017.08.089. Epub 2017 Aug 19. PubMed PMID: 28869847. 11: Vichapong J, Santaladchaiyakit Y, Burakham R, Srijaranai S. Ionic Liquid-Assisted Liquid-Liquid Microextraction based on the Solidification of Floating Organic Droplet in Sample Preparation for Simultaneous Determination of Herbicide Residues in Fruits. Acta Chim Slov. 2017 Sep;64(3):590-597. PubMed PMID: 28862309. 12: Wang Y, Li H, Feng G, Du L, Zeng D. Biodegradation of diuron by an endophytic fungus Neurospora intermedia DP8-1 isolated from sugarcane and its potential for remediating diuron-contaminated soils. PLoS One. 2017 Aug 15;12(8):e0182556. doi: 10.1371/journal.pone.0182556. eCollection 2017. PubMed PMID: 28809955; PubMed Central PMCID: PMC5557362. 13: Bai J, Han H, Wang F, Su L, Ding H, Hu X, Hu B, Li H, Zheng W, Li Y. Maternal linuron exposure alters testicular development in male offspring rats at the whole genome level. Toxicology. 2017 Aug 15;389:13-20. doi: 10.1016/j.tox.2017.07.005. Epub 2017 Jul 11. PubMed PMID: 28705778; PubMed Central PMCID: PMC5584558. 14: Spirhanzlova P, De Groef B, Nicholson FE, Grommen SVH, Marras G, Sébillot A, Demeneix BA, Pallud-Mothré S, Lemkine GF, Tindall AJ, Du Pasquier D. Using short-term bioassays to evaluate the endocrine disrupting capacity of the pesticides linuron and fenoxycarb. Comp Biochem Physiol C Toxicol Pharmacol. 2017 Oct;200:52-58. doi: 10.1016/j.cbpc.2017.06.006. Epub 2017 Jun 17. PubMed PMID: 28634053. 15: Kadar A, Peyre L, de Souza G, Wortham H, Doumenq P, Rahmani R. An accurate and robust LC-MS/MS method for the quantification of chlorfenvinphos, ethion and linuron in liver samples. Chemosphere. 2017 Oct;184:20-26. doi: 10.1016/j.chemosphere.2017.05.157. Epub 2017 May 29. PubMed PMID: 28577486. 16: Teixeira RR, de Andrade Barros MV, Bressan GC, Siqueira RP, Dos Santos FS, Bertazzini M, Kiralj R, Ferreira MMC, Forlani G. Synthesis, theoretical studies, and effect on the photosynthetic electron transport of trifluoromethyl arylamides. Pest Manag Sci. 2017 Nov;73(11):2360-2371. doi: 10.1002/ps.4623. Epub 2017 Aug 17. PubMed PMID: 28544262. 17: Karkanis A, Lykas C, Liava V, Bezou A, Petropoulos S, Tsiropoulos N. Weed interference with peppermint (Mentha x piperita L.) and spearmint (Mentha spicata L.) crops under different herbicide treatments: effects on biomass and essential oil yield. J Sci Food Agric. 2018 Jan;98(1):43-50. doi: 10.1002/jsfa.8435. Epub 2017 Jun 14. PubMed PMID: 28503740. 18: Kadar A, de Sousa G, Peyre L, Wortham H, Doumenq P, Rahmani R. Evidence of in vitro metabolic interaction effects of a chlorfenvinphos, ethion and linuron mixture on human hepatic detoxification rates. Chemosphere. 2017 Aug;181:666-674. doi: 10.1016/j.chemosphere.2017.04.116. Epub 2017 Apr 26. PubMed PMID: 28476006. 19: Eissa S, Zourob M. Selection and Characterization of DNA Aptamers for Electrochemical Biosensing of Carbendazim. Anal Chem. 2017 Mar 7;89(5):3138-3145. doi: 10.1021/acs.analchem.6b04914. Epub 2017 Feb 10. PubMed PMID: 28264568. 20: Nour EH, Elsayed TR, Springael D, Smalla K. Comparable dynamics of linuron catabolic genes and IncP-1 plasmids in biopurification systems (BPSs) as a response to linuron spiking. Appl Microbiol Biotechnol. 2017 Jun;101(11):4815-4825. doi: 10.1007/s00253-017-8135-6. Epub 2017 Feb 24. PubMed PMID: 28235988.