MedKoo Cat#: 558236 | Name: Anilazine
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Description:

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

Anilazine is a synthetic chlorinated triazine fungicide used to control fungal pathogens in crops like tomatoes, potatoes, and cereals. Its mechanism of action involves inhibition of mitochondrial respiration by disrupting electron transport in fungal cells, leading to energy depletion and cell death. While effective against a broad spectrum of fungi, anilazine has raised environmental and toxicological concerns, resulting in restricted or discontinued use in some regions.

Chemical Structure

Anilazine
Anilazine
CAS#101-05-3

Theoretical Analysis

MedKoo Cat#: 558236

Name: Anilazine

CAS#: 101-05-3

Chemical Formula: C9H5Cl3N4

Exact Mass: 273.9600

Molecular Weight: 275.52

Elemental Analysis: C, 39.23; H, 1.83; Cl, 38.60; N, 20.34

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
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Related CAS #
No Data
Synonym
Anilazine; Direz; Dyrene;
IUPAC/Chemical Name
1,3,5-Triazin-2-amine, 4,6-dichloro-N-(2-chlorophenyl)-
InChi Key
IMHBYKMAHXWHRP-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H5Cl3N4/c10-5-3-1-2-4-6(5)13-9-15-7(11)14-8(12)16-9/h1-4H,(H,13,14,15,16)
SMILES Code
ClC1=CC=CC=C1NC2=NC(Cl)=NC(Cl)=N2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 275.52 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
1: Faisal Manzoor M, Ali M, Muhammad Aadil R, Ali A, Goksen G, Li J, Zeng XA, Proestos C. Sustainable emerging sonication processing: Impact on fungicide reduction and the overall quality characteristics of tomato juice. Ultrason Sonochem. 2023 Mar;94:106313. doi: 10.1016/j.ultsonch.2023.106313. Epub 2023 Jan 25. PMID: 36739785; PMCID: PMC9932565. 2: Jeon Y, Kim J, Kang G, Kim TH. Crystal structure of anilazine. Acta Crystallogr Sect E Struct Rep Online. 2014 Aug 1;70(Pt 9):o923. doi: 10.1107/S160053681401647X. PMID: 25309255; PMCID: PMC4186163. 3: Jablonowski ND, Linden A, Köppchen S, Thiele B, Hofmann D, Burauel P. Dry-wet cycles increase pesticide residue release from soil. Environ Toxicol Chem. 2012 Sep;31(9):1941-7. doi: 10.1002/etc.1851. Epub 2012 Jul 27. PMID: 22782855; PMCID: PMC3465778. 4: Krajewski MP, Kanawati B, Fekete A, Kowalski N, Schmitt-Kopplin P, Grill E. Analysis of Arabidopsis glutathione-transferases in yeast. Phytochemistry. 2013 Jul;91:198-207. doi: 10.1016/j.phytochem.2012.04.016. Epub 2012 May 26. PMID: 22633844. 5: Jablonowski ND, Linden A, Köppchen S, Thiele B, Hofmann D, Mittelstaedt W, Pütz T, Burauel P. Long-term persistence of various 14C-labeled pesticides in soils. Environ Pollut. 2012 Sep;168:29-36. doi: 10.1016/j.envpol.2012.04.022. Epub 2012 May 15. PMID: 22591787. 6: Kaune A, Brüggemann R, Sharma M, Kettrup A. Soil Adsorption Coefficients of s-Triazines Estimated with a New Gradient HPLC Method. J Agric Food Chem. 1998 Jan 19;46(1):335-343. doi: 10.1021/jf9704930. PMID: 10554242. 7: Breithaupt DE, Schwack W. Photoinduced addition of the fungicide anilazine to cyclohexene and methyl oleate as model compounds of plant cuticle constituents. Chemosphere. 2000 Nov;41(9):1401-6. doi: 10.1016/s0045-6535(99)90553-2. PMID: 11057576. 8: Liebich J, Burauel P, Führ F. Microbial release and degradation of nonextractable anilazine residues. J Agric Food Chem. 1999 Sep;47(9):3905-10. doi: 10.1021/jf981274x. PMID: 10552742. 9: Lewalter J, Leng G. Consideration of individual susceptibility in adverse pesticide effects. Toxicol Lett. 1999 Jun 30;107(1-3):131-44. doi: 10.1016/s0378-4274(99)00040-5. PMID: 10414790. 10: Mathias CG. Allergic contact dermatitis from a lawn care fungicide containing dyrene. Am J Contact Dermat. 1997 Mar;8(1):47-8. PMID: 9066850. 11: Loosli R. Triazines. Toxicology. 1994 Jun 17;91(1):59-62. doi: 10.1016/0300-483x(94)90241-0. PMID: 8052987. 12: Oshiro Y, Piper CE, Balwierz PS, Soelter SG. Chinese hamster ovary cell assays for mutation and chromosome damage: data from non-carcinogens. J Appl Toxicol. 1991 Jun;11(3):167-77. doi: 10.1002/jat.2550110304. PMID: 1918790. 13: Schuman SH, Dobson RL. An outbreak of contact dermatitis in farm workers. J Am Acad Dermatol. 1985 Aug;13(2 Pt 1):220-3. doi: 10.1016/s0190-9622(85)70162-4. PMID: 2931456. 14: Garg FC, Tauro P, Mishra MM, Grover RK. Effect of fungicides on growth and on DNA, RNA and protein anabolism of a Rhizobium sp. Ann Microbiol (Paris). 1981 Sep-Oct;132B(2):231-9. PMID: 6173004. 15: Garg FC, Tauro P, Mishra MM, Grover RK. Effect of anilazine on growth, respiration and enzyme activity of Escherichia coli. Zentralbl Bakteriol Naturwiss. 1981;136(6):505-8. doi: 10.1016/s0323-6056(81)80097-3. PMID: 7034397. 16: Schuman SH, Dobson RL, Fingar JR. Dyrene dermatitis. Lancet. 1980 Dec 6;2(8206):1252. doi: 10.1016/s0140-6736(80)92515-5. PMID: 6108427. 17: Lawrence JF, Panopio LG. Comparison of gas and liquid chromatography for determination of anilazine in potatoes and tomatoes. J Assoc Off Anal Chem. 1980 Nov;63(6):1300-3. PMID: 7451394. 18: National Toxicology Program. Bioassay of anilazine for possible carcinogenicity (CAS No. 101-05-3). Natl Cancer Inst Carcinog Tech Rep Ser. 1978;104:1-115. PMID: 12799652. 19: Skjenneberg S, Jacobsen E, Movinkel H. pH-verdien i reinkjøtt etter forskjellig behandling av dyrene før slakting [pH-value in reindeer meat from different pre-slaughter treatment of the animals (author's transl)]. Nord Vet Med. 1974 Jul-Aug;26(7-8):436-43. Norwegian. PMID: 4473175. 20: Cohen SD, Murphy SD. Dyrene toxicity and lack of carboxylesterase inhibition in mice and rats. J Agric Food Chem. 1973 Jan-Feb;21(1):140-1. doi: 10.1021/jf60185a039. PMID: 4682330.