Simazine

Base Information

• Chemical Name: Simazine
• CAS No.: 122-34-9
• Deprecated CAS: 11141-20-1,119603-94-0,12764-71-5,39291-64-0,12764-71-5,39291-64-0
• Molecular Formula: C7H12ClN5
• Molecular Weight: 201.659
• Hs Code.: 29336990
• European Community (EC) Number: 204-535-2
• ICSC Number: 0699
• NSC Number: 25999
• UN Number: 3077,2588
• UNII: SG0C34SMY3
• DSSTox Substance ID: DTXSID4021268
• Nikkaji Number: J2.927K
• Wikipedia: Simazine
• Wikidata: Q416160
• Metabolomics Workbench ID: 51342
• ChEMBL ID: CHEMBL1605837
• Mol file: 122-34-9.mol

Synonyms:Herbazin 50;Herbazin-50;Herbazin50;Simazine

Chemical Property of Simazine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Melting Point: 225 °C
• Refractive Index: 1.622
• Boiling Point: 365.8 °C at 760 mmHg
• PKA: 2.71±0.10(Predicted)
• Flash Point: 175 °C
• PSA: 62.73000
• Density: 1.302 g/cm³
• LogP: 1.53460
• Storage Temp.: APPROX 4°C
• Water Solubility.: 0.0005 g/100 mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 201.0781231
• Heavy Atom Count: 13
• Complexity: 131
• Transport DOT Label: Class 9

Purity/Quality:

97% ^*data from raw suppliers

Simazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn;N,N,Xn,T,F
• Statements: 40-50/53-39/23/24/25-23/24/25-11-36-22
• Safety Statements: 36/37-46-60-61-45-26-16-7

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)NCC
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Uses: Simazine acts by inhibiting photosynthesis. It is an active ingredient in Aquazine, Cekusan, Gesatop, Primatol/S, Princep, Simades, and Simanex. This herbicide is used primarily on fruit and maize and at industrial and aquatic sites, including near swimming pools and cooling towers. It typically is found as an 80% wettable powder or a 90% granule. S-triazine herbicide. It is easily adsorbed on the surface by soil to form a poisonous soil layer, which can kill the roots of shallow-rootedness weeds seedling. The effect on perennial or deep rooted weeds with deep roots is poor. It is used to prevent annual or biennial broadleaf and most monocotyledonous weeds which are propagated by seeds for corn, sugarcane, sorghum, tea, rubber, orchard and nursery. It has obvious inhibiting effects on perennial weeds that are propagated by rhizomes or roots. It can be used as a sterilant herbicide for forest firebreaks, railroad bed lines, courtyards, storage areas in warehouse, tank farms, woodyards and so on by increasing the dose. Suggested use: corn 30 to 60g/100m2 (summer corn 15 to 30g/100m2), sorghum 30 to 66g/100 m2, sugarcane 22.5 to 30g/100 m2, tea 22.5 to 37.5g/100 m2, rubber 45 to 67.6g/100 m2, orchard 45 to 75g/100 m2, nursery garden 1 to 2g per square meter. It is added into water for the suspension for to spray on the soil surface. Selective preemergence systemic herbicide used to control many broad-leaved weeds and annual grasses in deep-rooted fruit and vegetable crops. Simazine is a preemergence herbicide used to control broadleaf and grassy weeds. It is also used as a soil sterilant. Principal crops involved include maize, citrus, and deciduous fruit. Simazine is also used in aquatic weed control. Xenoestrogens are used widely in a number of cosmetic products such as plasticizers, perfume fixatives, and solvents (e.g., dibutyl phthalate); and industrial chemicals and pollutants such as insecticides (e.g., methoxychlor, DDT, and DDE), epoxy resins, polycarbonate (e.g., bisphenol A), other plastics (e.g., butyl benzyl phthalate (BBP)), and herbicides (e.g., simazine). Compounds in this group exhibit a broad molecular and structural diversity, often mimicking the activities of naturally occurring hormones, since they are recognized by the hormone’s cognate receptor protein. Many compounds in this group of chemicals have been classified as environmental EDCs, defined by the US Environmental Protection Agency (EPA) as “an exogenous agent that interfere with synthesis, secretion, transport, metabolism, binding action, or elimination of natural blood-borne hormones that are present in the body and are responsible for homeostasis, reproduction and developmental processes.” However, not all EDCs are classified as xenoestrogens. Although relative binding affinities (RBAs) of a number of compounds exhibiting xenoestrogenic activities, it should be noted that the values appearing here and in the reports listed under Further Reading are highly dependent on the type of ER-based assay used and the concentration of the compound tested. In addition, caution should be exercised in interpreting the results from assays performed in vitro compared to effects observed in vivo. Duration of exposure and dose in vivo, which are likely influenced by the lipophilic properties of many of the agents, should be considered in health risk assessment. In summary, the body of experimental and epidemiological evidence suggesting that many substances in the environment may disrupt human health continues to expand to cover a wide range of exposures. Of greatest concern are the effects of transgenerational exposure to unrecognized agents, which may be present in foodstuffs, drinking water, and other consumables, including medications and cosmetics. Using hormone receptor-based technology and highly purified preparations of EDCs as standards, there is an opportunity to improve exposure and risk assessment for environmental estrogen mimics, as well as the quantitative analysis of their occurrence in the environment. However, discussions continue regarding the relationships between assessment in vitro of xenoestrogen activities and their effects in vivo resulting in a risk to health.
• Description: While compounds exhibiting estrogen mimicry are structurally diverse, they share common properties such as retention in body fat deposits (highly lipophilic), ability to cross the placental barrier, transport in blood usually unbound to specialized serum proteins (e.g., steroid hormone binding globulin, SHBG/TeBG), and their affinity for the estrogenreceptor protein. If the environmental compound impersonates estrogen sufficiently, it associates with the estrogen-receptor protein and either disrupts the action of the native hormone or communicates activities similar to estrogen (i.e., antagonistic or agonistic activities). Association between a xenoestrogen and the estrogen receptor (ER), characterized by a wide range of affinities, is reversible and saturable. No metabolism of the ligand occurs when it is bound to the receptor protein. In addition to the phenotypic expression of gender, estrogens and their mimics may influence development and physiological processes in many organs of the body, particularly the reproductive tract, as well as the central nervous system and skeleton. It is obvious that fragile, biological events occurring during ovulation, pregnancy, fetal development, and lactation could easily be influenced by xenoestrogens with endocrine disruptor compound (EDC) activities, which mimic naturally occurring hormones. With a variety of sensitive, rapid assays, xenoestrogens now may be detected and activities assessed by ER proteins. The range of techniques available includes both cell-free and whole-cell-based assays: 1. Rat uterine cytosol preparations containing ERs (a cell-free assay using radiolabeled ligand); 2. Recombinant human ER proteins produced by a bacteria, yeast, or baculovirus-infected insect cell system (cell-free assays using radiolabeled ligand); 3. A yeast cell system containing recombinant human ER and a reporter gene (yeast whole-cell assay); 4. The LUMI-CELL ER transcriptional activation assay (BG1Luc ER TA, a mammalian whole-cell assay); and 5. MCF7 cell proliferation assay (E-SCREEN assay) and modifications of this method (mammalian whole-cell assay). Additionally, certain investigations are focused on differential recognition of EDCs by ER isoforms separated by highperformance liquid chromatography.

Technology Process of Simazine

There total 3 articles about Simazine 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: 92.0%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + ethylamine (75-04-7,85404-22-4) → Simazine (122-34-9)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 - 50 ℃; for 1.5h;

Reference yield:

2-ethylamino-4,6-dichloro-[1,3,5]triazine (3440-19-5) + ethylamine (75-04-7,85404-22-4) → Simazine (122-34-9)

Guidance literature:

With sodium hydroxide; In water; at 25 - 40 ℃;

Reference yield:

→ Simazine (122-34-9)

Guidance literature:

upstream raw materials:

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

ethylamine

2-ethylamino-4,6-dichloro-[1,3,5]triazine

Downstream raw materials:

2,4-bis(ethylamino)-6-hydrazino-s-triazine

α-SETOH

Deisopropylatrazine

β-SETOH

Refernces

• 1、 Alvani, Mohsen,Asadi, Parvin,Hajhashemi, Valiollah,Khodarahmi, Ghadamali,Rostami, Mahboubeh. "Design, synthesis, biological evaluation, and molecular docking study on triazine based derivatives as anti-inflammatory agents". . . Retrieved 2021/07/01.
• 2、 Zheng, Xiao-Zhu,Zhou, Jia-Li,Ye, Jing,Guo, Pei-Pei,Lin, Chun-Shui. "Cardioprotective effect of novel sulphonamides-1,3,5-triazine conjugates against ischaemic–reperfusion injury via selective inhibition of MMP-9". . p. 756 - 765. Retrieved 2016/10/19.