Atrazine

Base Information

• Chemical Name: Atrazine
• CAS No.: 1912-24-9
• Deprecated CAS: 11121-31-6,12040-45-8,12797-72-7,39400-72-1,69771-31-9,93616-39-8,12040-45-8,39400-72-1,69771-31-9,93616-39-8
• Molecular Formula: C8H14ClN5
• Molecular Weight: 215.686
• Hs Code.: 29336990
• European Community (EC) Number: 217-617-8
• ICSC Number: 0099
• NSC Number: 163046
• UN Number: 2763
• UNII: QJA9M5H4IM
• DSSTox Substance ID: DTXSID9020112
• Nikkaji Number: J3.685D
• Wikipedia: Atrazine
• Wikidata: Q408652
• Metabolomics Workbench ID: 49565
• ChEMBL ID: CHEMBL15063
• Mol file: 1912-24-9.mol

Synonyms:Atrazine;Gesamprim

Chemical Property of Atrazine

Chemical Property:

• Appearance/Colour: colourless crystals or white powder
• Vapor Pressure: 0.00156mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.589
• Boiling Point: 368.5 °C at 760 mmHg
• PKA: pKa 1.64 (Uncertain)
• Flash Point: 176.7 °C
• PSA: 62.73000
• Density: 1.269 g/cm³
• LogP: 1.92310
• Storage Temp.: APPROX 4°C
• Water Solubility.: Slightly soluble. 0.007 g/100 mL
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 215.0937732
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

97% tech ^*data from raw suppliers

Atrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn;N,N,Xn,T,F,Xi
• Statements: 43-48/22-50/53-39/23/24/25-23/24/25-11-38-36/37/38-20/21/22-52/53
• Safety Statements: 2-36/37-60-61-45-16-7-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Triazine
• Canonical SMILES: CCNC1=NC(=NC(=N1)Cl)NC(C)C
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes.
• Effects of Long Term Exposure: The substance may have effects on the liver. This may result in tissue lesions.
• Description: Atrazine appears as an odorless white powder, belonging to a selective triazine herbicide. It can be used for stopping the growth of broadleaf and grassy weeds associated with crops including sorghum, maize, sugarcane, lupins, pine, eucalypt plantations and triazine-tolerant canola. According to the statistics of US in 2014, it ranks 2nd as one of the most widely used herbicide, only after glyphosate. Atrazine exerts its effect through targeting on the photosynthesis II system of the weeds, blocking the photosynthesis process and causing the death of weeds. It could be manufactured through the treatment of cyanuric chloride with ethylamine and isopropyl amine. However, it has been shown that it has certain toxicity on humans and other animals through targeting on the endocrine systems. A major effort in evaluating the toxicity of the triazines is the cumulative risk assessment (CRA) conducted by US Environmental Protection Agency (EPA) as part of the tolerance reassessment process under the Food Quality Protection Act (FQPA) of 1996. The CRA (released 2006) was conducted for triazines as a common mechanism group (CMG), determined to have a ‘common mechanism of toxicity’ in acting the same way in the body, that is, the same toxic effect occurs in the same organ or tissue by essentially the same sequence of major biochemical events. EPA determined that atrazine, simazine, propazine, and the metabolites desethyl-s-atrazine (DEA), desisopropyl-s-atrazine (DIA), and diaminochlorotriazine (DACT) are considered as a CMG due to their ability to cause neuroendocrine- and endocrine-related developmental, reproductive, and carcinogenic effects. Other triazines, such as ametryn, prometryn, prometon, metsulfuron methyl, trisulfuron, chlorsulfuron, and DPX-M6316, were excluded because these triazines do not share the toxicity profile of the CMG triazines. Hydroxyatrazine was excluded based on the lack of mammary tumor induction and no compelling evidence of neuroendocrine-related toxicity. Propazine was excluded from the cumulative assessment group (CAG) because exposures to propazine are not anticipated via any of the relevant exposure pathways. Therefore, the cumulative assessment included only atrazine, simazine, DEA, DIA, and DACT, referred to as ‘triazine residues.’ For the triazines, the major toxicity of concern involves the neuroendocrine system with the key toxicity mechanism being luteinizing hormone (LH)-dependent effects. The changes in circulating endocrine hormones regardless of rat strain is the basis for assuming commonality of mechanism, which were noted in the same range of doses for these triazines. The relevance of the induction of mammary tumors in female Sprague–Dawley (SD) rats to humans continues to be a subject of discussion and research on the endocrine effects of triazines. Another consideration is whether the chemicals’ effects on endocrine responses have an impact on reproduction, development, and the brain related or unrelated to carcinogenesis. Significant research into the mechanism of mammary tumor formation was conducted in which the effects of atrazine, simazine, and other triazines were studied on estrus cycle, estrogen-mediated responses, estrogen receptor binding, and hormonal induction and metabolism in several species, but mostly in the rat. Both the in vivo and in vitro data suggest that atrazine and simazine disrupt ovarian cycling and induce mammary tumors in female SD rates, and alteration of the estrous state is directly associated with the incidence of mammary tumors. Atrazine and its metabolites appear to affect reproductive function of the male as well as the female reproductive and development parameters. However, they have not been tested with exposure at all critical periods of development in the young, evaluated in standard guideline neurotoxicity assay, and the earlier reproductive toxicity studies did not include sensitive measures of endocrine disruption that are now included. Additional studies have been published since the CRA in 2006. The US EPA FIFRA panel reevaluated the database and reaffirmed the conclusion on the toxicity of the triazines and the mammary tumor determination in 2010.
• Uses: Atrazine is used as a selective herbicide to control broadleaf and grassy weeds for agriculture and other land not used for crops. In agriculture, atrazine is used on corn, sugarcane, and pineapple and for orchards, sod, tree plantations, and rangeland. Atrazine is moderately persistent in the environment because of its low solubility. It can be detected in the water table and in the upper layers of the soil profile in many areas (Huang and Frink, 1989). The Environmental Protection Agency (EPA) reported that atrazine was one of the two most commonly used agricultural herbicides in 2007 (EPA, 2011). It is an active ingredient in many brands, including Actinite PK, Atranex, Atrasine, Atrataf, Atrazin, Chromozin, Cyazin, Primatol A, Primase, AAtre, Griffex, and Weedex. Preemergence and postemergence herbicide for control of some annual grasses and broad-leaved weeds in corn, fallow land, rangeland, sorghum, non-cropland, certain trop ical plantations, evergreen nurseries, fruit crops and lawns. Atrazine is widely used as a selective herbicide to control broadleaf and grassy weeds in corn, sorghum, rangeland, sugarcane, orchards, pineapple, and turf grass sod. It is also used for selective weed control in conifer restoration and Christmas tree plantations. It is also used as a nonselective herbicide for vegetation control in noncrop land. Chlorotriazine herbicides have the characteristic triazine (three-nitrogen) aromatic ring, with one chlorine substituent. Chloro-s-triazines may have substitution at the R1 (2 position) by chlorine, thiomethyl, or methoxy. The more extensively studied ones include atrazine (6-chloro-N-ethyl-N0-isopropyl- 1,3,5-triazine-2,4-diamine), simazine (2-chloro-4,6-bis (ethylamino)-s-triazine), propazine (2-chloro-4,6-bis (isopropylamino)-s-triazine), and terbuthylazine (2-(tertbutylamino)- 4-chloro-6-(ethylamino)-s-triazine). Atrazine and simazine are selective pre- and postemergence herbicides used on crops for control of broad leaf and grassy weeds and in rights-of-way maintenance. Atrazine, first marketed in 1957, is widely used on cauliflower, corn, sorghum, and sugarcane, and in noncropped areas such as wheat fallow. Simazine, introduced in 1956, is used on corn, almonds, grapes, and oranges. Major triazine use occurs in the midwestern cornbelt region of the United States.

Technology Process of Atrazine

There total 3 articles about Atrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.6%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + ethylamine (75-04-7,85404-22-4) + isopropylamine (75-31-0) → 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9,93616-39-8)

Guidance literature:

1,3,5-trichloro-2,4,6-triazine; With potassium chloride; sodium chloride; potassium bromide; magnesium chloride; In water; at 3 ℃; for 0.233333h;

isopropylamine; In water; at 0 - 15 ℃; for 1.08333h;

ethylamine; Further stages;

Reference yield: 83.5%

2,4-dichloro-6-isopropylamino-1,3,5-triazine (3703-10-4) + ethylamine (75-04-7,85404-22-4) → 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9,93616-39-8)

Guidance literature:

With sodium hydroxide; In water; toluene; at 15 - 20 ℃; for 0.25h;

DOI:10.1021/jf203383s

Reference yield:

→ 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9,93616-39-8)

Guidance literature:

upstream raw materials:

2,4-dichloro-6-isopropylamino-1,3,5-triazine

ethylamine

1,3,5-trichloro-2,4,6-triazine

isopropylamine

Downstream raw materials:

2-Chloro-4,6-diamino-1,3,5-triazine

Deisopropylhydroxyatrazine

Deethylatrazine

Hydroxyatrazine

Refernces

• 1、 -. "Novel water method synthetic process of atrazine". Paragraph 0038-0039. . Retrieved 2017/02/28.
• 2、 -. "N,N-dinitramide salts as solubilizing agents for biologically active agents". . . Retrieved 2008/06/13.