| Identification | More | [Name]
Simazine | [CAS]
122-34-9 | [Synonyms]
1-CHLORO-2,3-BIS(METHYLTHIO)BENZENE
1-Chloro-3,5-bisethylamino-2,4,6-triazine
2,4-BIS(ETHYLAMINO)-6-CHLORO-1,3,5-TRIAZINE
2,4-bis(ethylamino)-6-chloro-s-triazine
2 4-BIS(ETHYLAMINO)-6-CHLORO-SYM-TRIAZINE
2-CHLORO-4,6-BIS(ETHYLAMINO)-1,3,5-TRIAZINE
2-CHLORO-4,6-BIS(ETHYLAMINO)-S-TRIAZINE
2-CHLORO-4,6-BIS(ETHYLAMINO)-SYM-TRIAZINE
2-Chloro-4，6-di(ethylamine)-1，3，5-triazine
AMIZINA
AMIZINE
CALIBER
CAT
CDT(R)
CET(R)
G-27692(R)
GESAPUN
GESATOP
GESATOP(R)
LUSERB | [EINECS(EC#)]
204-535-2 | [Molecular Formula]
C7H11ClN4 | [MDL Number]
MFCD00023174 | [Molecular Weight]
186.64 | [MOL File]
122-34-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Simazine is a combustible, white crystalline solid. Practically odorless. | [Melting point ]
225°C | [Boiling point ]
329.54°C (rough estimate) | [density ]
1.302 | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
1.6110 (estimate) | [Fp ]
100 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
DMF: slightly soluble,DMSO: slightly soluble | [form ]
Crystals | [pka]
2.71±0.10(Predicted) | [color ]
White | [Water Solubility ]
0.0005 g/100 mL | [Merck ]
14,8533 | [BRN ]
10895 | [Exposure limits]
ACGIH: TWA 0.5 mg/m3; TWA 2 mg/m3 | [LogP]
2.18 at 20℃ | [Dissociation constant]
1.49-1.75 at 20℃ | [CAS DataBase Reference]
122-34-9(CAS DataBase Reference) | [IARC]
3 (Vol. 53, 73) 1999 | [NIST Chemistry Reference]
1,3,5-Triazine-2,4-diamine, 6-chloro-N,N'-diethyl-(122-34-9) | [EPA Substance Registry System]
122-34-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn,T,F | [Risk Statements ]
R40:Limited evidence of a carcinogenic effect.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S46:If swallowed, seek medical advice immediately and show this container or label .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
3077 | [WGK Germany ]
3 | [RTECS ]
XY5250000 | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29336990 | [Hazardous Substances Data]
122-34-9(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 5000 mg/kg (Bailey, White) |
| Hazard Information | Back Directory | [General Description]
White to off-white crystalline powder. | [Reactivity Profile]
SIMAZINE(122-34-9) is hydrolyzed by strong acids and alkalis . | [Air & Water Reactions]
Insoluble in water. | [Potential Exposure]
A potential danger to those involved in the manufacture, formulation, and application of this preemergence herbicide. Pesticide not in use; TRI and/or IUR indicates importers or manufacturers are unlikely. Banned for use in the EU. | [Fire Hazard]
Literature sources indicate that this chemical is nonflammable. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. UN2763 Triazine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | [Incompatibilities]
Powder may form explosive mixture with air. Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. | [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. | [Waste Disposal]
Strong acid or alkaline hydrolysis leads to complete degradation of simazine. However,large quantities of simazine should be incinerated in a unit operating @ 850℃ equipped with off-gas scrubbing equipment. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. | [Definition]
ChEBI: A diamino-1,3,5-triazine that is N,N'-diethyl-1,3,5-triazine-2,4-diamine substituted by a chloro group at position 6. | [Production Methods]
Simazine is prepared by reacting two equivalents of ethylamine
in the presence of an acid acceptor. It is stable in neutral
and slightly basic or acidic media, but is hydrolyzed by
stronger acids and bases especially at higher temperatures.
Primary exposures occur during application, not during
production, and include both inhalation and dermal components. | [Health Hazard]
Inconsistent data in the literature; oral LD50values in rats reported as 970 and 5000 mg/L,showing a wide difference; toxicity is of loworder. | [Agricultural Uses]
Pre-emergence herbicide, Algaecide: and ornamental crops, turf grass, orchards, and vineyards. At higher rates, it is used for non-selective weed control in industrial areas. Before 1992, simazine was used to control submerged weeds and algae in large aquariums, farm ponds, fish hatcheries, swimming pools, ornamental ponds, and cooling towers. Simazine is available in wettable powder, waterdispersible granule, liquid, and granular formulations. It may be soil-applied. Not approved for use in EU countries. A U.S. EPA restricted Use Pesticide (RUP) for all land uses because of its potential to contaminate ground water | [Trade name]
AKTINIT S®; ALCO® Simizine; AQUAZINE®; ATLAS SIMAZINE®; BATAZINA®; BITEMOL®; CALIBER®; CDT®; CEKUSAN®; CEKUZINA-S®; FRAMED®; G 27692®; GEIGY 27692®; GESARAN®; GESATOP®; GESATOP-50®; H 1803®; HARLEQUIN®; HERBAZIN® 500 BR; HERBAZIN® 50; HERBEX®; HERBOXY®; HUNGAZIN DT®; OXON ITALIA SIM-TROL®; PREMAZINE®; PRIMATEL S®; PRIMATOL S®; PRINCEP®; PRINCEP® 80W; SIMADEX®; SIMANEX®; SIMAZINE® 80W; SIMAZAT®; SIM-TROL®; TAFAZINE®; TAFAZINE® 50-W; TANZINE®; TAPHAZINE®; TOTAZINE®; TRIAZINE A 384®; W 6658®; WEEDEX®; ZEAPUR® | [Carcinogenicity]
No tumorigenic response was
seen in mice treated orally at doses ranging from 75 to
215mg/kg. In a 2-year feeding study in rats, 100 ppm
produced mammary tumors. Sarcomas at the injection
sitewere produced in another study ofboth rats and mice.
Simazinewas fedtoratsatdoselevelsequivalent to 0,0.5,5,and
50mg/kg for 2 years.Bodyweight and hematological changes
were seen primarily at the highest dose. After 24 months at
50mg/kg, an increase in ovarian atrophy and Sertoli cell
hyperplasia were seen. Increases in mammary gland tumors
were seen in females at 50mg/kg. | [Environmental Fate]
Soil. The reported half-life in soil is 75 days (Alva and Singh, 1991). Under laboratory
conditions, the half-lives of simazine in a Hatzenbühl soil (pH 4.8) and Neuhofen soil (pH
6.5) at 22°C were 45 and 100 days, respectively (Burkhard and Guth, 1981).
The half-lives for simazine in soil incubated in the laboratory under aerobic conditions
ranged from 27 to 231 days (Zimdahl et al., 1970; Beynon et al., 1972; Walker, 1976,
1976a). In field soils, the disappearance half-lives were lower and ranged from 11 to 91
days (Roadhouse and Birk, 1961; Clay, 1973; Joshi and Datta, 1975; Marriage et al., 1975).
Groundwater. According to the U.S. EPA (1986) simazine has a high potential to leach
to groundwater.
Plant. Simazine is metabolized by plants to the herbicidally inactive 6-hydroxysimazine which is further degraded via dealkylation of the side chains and hydrolysis of
the amino group releasing carbon dioxide (Castelfranco et al., 1961; Humburg et al., 1989).
Photolytic. Pelizzetti et al. (1990) studied the aqueous photocatalytic degradation of
simazine and other s-triazines (ppb level) using simulated sunlight (λ >340 nm) and
titanium dioxide as a photocatalyst. Simazine rapidly degraded forming cyanuric acid,
nitrates and other intermediate compounds similar to those found for atrazine. Mineralization of cyanuric acid to carbon dioxide was not observed (Pelizzetti et al., 1990). In
aqueous solutions, simazine is converted exclusively to hydroxysimazine by UV light (λ
= 253.7 nm). The UV irradiation of methanolic solutions of simazine afforded simetone
(2-methoxy-4,6-bis(ethylamino-s-triazine). Photodegradation of simazine in methyl alcohol did not occur when irradiated at wavelengths >300 nm (Pape and Zabik, 1970).
Chemical/Physical. Emits toxic fumes of nitrogen oxides and chlorine when heated
to decomposition (Sax and Lewis, 1987). In the presence of hydroxy or perhydroxy radicals
generated from Fenton’s reagent, simazine undergoes dealkylation to give 2-chloro-4,6-
diamino-s-triazine as the major product (Kaufman and Kearney, 1970). | [Toxicity evaluation]
With regard to estrogen-associated toxicity, the primary
mechanism appears to be via association with the estrogen receptor proteins (ERa and ERb) and subsequent alteration in
the signal transduction pathway. While largely acting as
estrogen antagonists, some xenoestrogens (e.g., diethylstilbestrol
(DES)) may act as agonists at low doses and antagonists at
elevated doses. Furthermore, compounds such as DES are
classified as an EDC since it may promote transgenerational
effects, including development of clear cell adenocarcinoma of
the vagina in daughters of mothers administered DES as
a therapeutic.
Many studies of toxicokinetics suggest the difficulty in
extrapolating quantitative structure–activity relationships
(QSARs) of particular compounds with their influence on
biological responses (e.g., reproduction, neuroendocrine behavior).
Several compounds classified as xenoestrogens (BPA
and BBP) are reported to have estrogenic activity, although the
concentrations required in vitro for the effects and those doses
given in vivo to animal models are significantly higher than the
estimated doses observed in human exposure. The variety of ERbased
tests for assessing QSARs of diverse xenoestrogens cannot
address the effects of long-term exposure to low doses of these
compounds. In addition, factors such as age at exposure and
mixtures of compounds influence latent effects of chronic
exposure. However, QSAR models using results from ER-based
tests are used for chemical risk management and development
of regulatory practices. |
| Questions And Answer | Back Directory | [Chemical Properties]
Simazine (2-chloro-4,6-bis(ethylamino)-s-triazine) is a selective, herbicide that inhibits photosynthesis. It occurs as awhite crystalline solid, soluble at 5 ppm(at20–22 °C) in water and 400 ppm in methanol. The vapor pressure of simazine is 0.0000000061mmHg (at 20 °C [68°F]).
| [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. | [Synthesis]
The product is obtained by the reaction between triazine cypermethrin and ethylamine in the presence of acid acceptor. If using water as the reaction medium, add materials at 0℃, then hold temperature and stir at 70℃ for 2h. If the reaction is carried out in the solvents like trichloroethylene, the reaction temperature is between 30℃ and 50℃. The consumption figures of raw materials: cyanuric chloride (96%), 1020kg/t (100% 520kg/t) ethylamine, liquid (40%) 100kg/t, trichloroethylene (industrial products) 120kg/t.
| [Category]
Pesticide
| [Toxicity grading]
Medium toxicity | [Acute toxicity]
Orally - rat LD50: 971 mg / kg; orally - mice LD50: 5000 mg / kg
| [Irritation]
Skin- A rabbit 500 mg light
| [Flammability Hazard]
Toxic nitrogen oxides and chloride gases are produced by combustion; toxic reaction: emaciation and the decrease of red blood cells.
| [Storage]
Store it in low temperature, dry and ventilated environment.
| [Extinguishant]
Dry powder, foam, sand.
| [Professional standard]
TWA 5mg/m3 |
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