Napropamide | CAS#15299-99-7 | herbicide

MedKoo Cat#: 461084 | Name: Napropamide

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Description:

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

Napropamide belongs to the amide herbicide family and widely used to control weeds in farmland.

Chemical Structure

Napropamide

CAS#15299-99-7

Theoretical Analysis

MedKoo Cat#: 461084

Name: Napropamide

CAS#: 15299-99-7

Chemical Formula: C17H21NO2

Exact Mass: 271.1572

Molecular Weight: 271.36

Elemental Analysis: C, 75.25; H, 7.80; N, 5.16; O, 11.79

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 230.00

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Synonym

Napropamide; Devrinol; Waylay; R 7465; R-7465; R7465;

IUPAC/Chemical Name

N,N-diethyl-2-(naphthalen-1-yloxy)propanamide

InChi Key

WXZVAROIGSFCFJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3

SMILES Code

CC(OC1=C2C=CC=CC2=CC=C1)C(N(CC)CC)=O

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Napropamide is a selective systemic amide herbicide used to control a number of annual grasses and broad-leaved weeds.

In vitro activity:

To investigate this, this study has examined the inhibition effect of napropamide on Echinochloa crus-galli mono-cultured or co-cultured with maize at field conditions. These results on morphology, physiology, chlorophyll content and chlorophyll fluorescence suggest that R-napropamide has stronger inhibitory effect than Rac-napropamide and S-napropamide on Echinochloa crus-galli, while none of them affects maize. Reference: Sci Total Environ. 2019 Sep 10;682:151-159. https://pubmed.ncbi.nlm.nih.gov/31112816/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	42.0	154.78

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 271.36 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. Xie J, Tang W, Zhao L, Liu S, Liu K, Liu W. Enantioselectivity and allelopathy both have effects on the inhibition of napropamide on Echinochloa crus-galli. Sci Total Environ. 2019 Sep 10;682:151-159. doi: 10.1016/j.scitotenv.2019.05.058. Epub 2019 May 7. PMID: 31112816. 2. Shen Y, Zhang J, Xie J, Liu J. In vitro assessment of corticosteroid effects of eight chiral herbicides. J Environ Sci Health B. 2020;55(2):91-102. doi: 10.1080/03601234.2019.1665408. Epub 2019 Sep 16. PMID: 31524045.

In vitro protocol:

In vivo protocol:

TBD

1: Qi Y, Liu D, Zhao W, Liu C, Zhou Z, Wang P. Enantioselective phytotoxicity and bioacitivity of the enantiomers of the herbicide napropamide. Pestic Biochem Physiol. 2015 Nov;125:38-44. doi: 10.1016/j.pestbp.2015.06.004. Epub 2015 Jun 13. Review. PubMed PMID: 26615149. 2: Qi Y, Liu D, Sun M, Di S, Wang P, Zhou Z. The chiral separation and enantioselective degradation of the chiral herbicide napropamide. Chirality. 2014 Feb;26(2):108-13. doi: 10.1002/chir.22277. Epub 2014 Jan 17. PubMed PMID: 24436218. 3: Cho S, Kim J, Jeon Y, Kim TH. Napropamide. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 6;69(Pt 8):o1207. doi: 10.1107/S1600536813017947. eCollection 2013. PubMed PMID: 24109304; PubMed Central PMCID: PMC3793717. 4: Sadegh-Zadeh F, Wahid SA, Seh-Bardan BJ, Othman R, Omar D. Fate of napropamide herbicide in selected Malaysian soils. J Environ Sci Health B. 2012;47(2):144-51. doi: 10.1080/03601234.2012.624481. PubMed PMID: 22251214. 5: Cui LE, Yang H. Accumulation and residue of napropamide in alfalfa (Medicago sativa) and soil involved in toxic response. J Hazard Mater. 2011 Jun 15;190(1-3):81-6. doi: 10.1016/j.jhazmat.2011.02.086. Epub 2011 Mar 6. PubMed PMID: 21439724. 6: Zhang C, Wu XM, Long YH, Li M, Li RY, Yin XH. [Identification and degradation characteristics of a napropamide-degrading bacterium strain]. Ying Yong Sheng Tai Xue Bao. 2016 Oct;27(10):3371-3378. doi: 10.13287/j.1001-9332.201610.017. Chinese. PubMed PMID: 29726165. 7: Zhang R, Cui J, Zhu HM, Yang H. Effect of dissolved organic matters on napropamide availability and ecotoxicity in rapeseed ( Brassica napus ). J Agric Food Chem. 2010 Mar 10;58(5):3232-40. doi: 10.1021/jf9027766. PubMed PMID: 20143852. 8: Guo H, Chen G, Lv Z, Zhao H, Yang H. Alteration of microbial properties and community structure in soils exposed to napropamide. J Environ Sci (China). 2009;21(4):494-502. PubMed PMID: 19634425. 9: Cui J, Zhang R, Wu GL, Zhu HM, Yang H. Salicylic acid reduces napropamide toxicity by preventing its accumulation in rapeseed (Brassica napus L.). Arch Environ Contam Toxicol. 2010 Jul;59(1):100-8. doi: 10.1007/s00244-009-9426-4. Epub 2009 Dec 5. PubMed PMID: 19967348. 10: Xie J, Zhao L, Liu K, Guo F, Liu W. Enantioseparation of four amide herbicide stereoisomers using high-performance liquid chromatography. J Chromatogr A. 2016 Nov 4;1471:145-154. doi: 10.1016/j.chroma.2016.10.029. Epub 2016 Oct 13. PubMed PMID: 27760706. 11: Liu H, Dang Y, Zhang S, Liu H, Qu L, Liao X, Zhao Y, Wu Y. Determination of diphenamide, napropamide and metolachlor in tobacco by gel permeation chromatographic clean-up and high performance liquid chromatography. Ann Chim. 2005 May;95(5):369-74. PubMed PMID: 16477944. 12: Williams CF, Letey J, Farmer WJ. Molecular weight of dissolved organic matter-napropamide complex transported through soil columns. J Environ Qual. 2002 Mar-Apr;31(2):619-27. PubMed PMID: 11931454. 13: Pahari AK, Majumdar S, Mandal TK, Chakraborty AK, Bhattacharyya A, Chowdhury A. Toxico-kinetics, recovery, and metabolism of napropamide in goats following a single high-dose oral administration. J Agric Food Chem. 2001 Apr;49(4):1817-24. PubMed PMID: 11308331. 14: Da Silva JP, Bastos EV, Ferreira LF, Weiss RG. Surface photochemistry of the herbicide napropamide. The role of the media and environmental factors in directing the fates of intermediates. Photochem Photobiol Sci. 2008 Jan;7(1):69-75. doi: 10.1039/b713369c. Epub 2007 Oct 31. PubMed PMID: 18167599. 15: Antonious GF, Patterson MA. Napropamide residues in runoff and infiltration water from pepper production. J Environ Sci Health B. 2005;40(3):385-96. PubMed PMID: 15913012. 16: Guo H, Zhu HM, Yang H. [Degradation and adsorption behavior of napropamide in soils]. Huan Jing Ke Xue. 2008 Jun;29(6):1729-36. Chinese. PubMed PMID: 18763531. 17: Salinas-Castillo A, Fernández-Sanchez JF, Segura-Carretero A, Fernández-Gutiérrez A. Simple determination of the herbicide napropamide in water and soil samples by room temperature phosphorescence. Pest Manag Sci. 2005 Aug;61(8):816-20. PubMed PMID: 15838936. 18: Biswas PK, Pramanik SK, Mitra SR, Bhattacharyya A. Persistence of napropamide in/on tea under North-East Indian climatic condition. Bull Environ Contam Toxicol. 2007 Nov;79(5):566-9. Epub 2007 Oct 9. PubMed PMID: 17924045. 19: Li YN, Wu HL, Qing XD, Nie CC, Li SF, Yu YJ, Zhang SR, Yu RQ. The maintenance of the second-order advantage: second-order calibration of excitation-emission matrix fluorescence for quantitative analysis of herbicide napropamide in various environmental samples. Talanta. 2011 Jul 15;85(1):325-32. doi: 10.1016/j.talanta.2011.03.067. Epub 2011 Apr 5. PubMed PMID: 21645706. 20: Chen SW, Cai XY, Xi M, Zhang AP, Liu WP. [Characterization of napropamide enantiomers by CD and determination of the enantiomeric ratios in water]. Guang Pu Xue Yu Guang Pu Fen Xi. 2006 Sep;26(9):1649-52. Chinese. PubMed PMID: 17112038.