122-34-9 Usage
Uses
Used in Agricultural Industry:
Simazine is used as a pre-emergence herbicide for the control of many broad-leaved weeds and annual grasses in deep-rooted fruit and vegetable crops. It is also used as an algaecide and for ornamental crops, turf grass, orchards, and vineyards. At higher rates, it is used for non-selective weed control in industrial areas.
Simazine is used as a preemergence herbicide for the control of broadleaf and grassy weeds, primarily on fruit and maize. It is also used as a soil sterilant and is effective against 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.
Used in Aquatic Weed Control:
Simazine is used in aquatic weed control, including near swimming pools and cooling towers. Before 1992, it was used to control submerged weeds and algae in large aquariums, farm ponds, fish hatcheries, and ornamental ponds.
Used in Cosmetic Products:
Simazine is used as a component in a number of cosmetic products, such as plasticizers, perfume fixatives, and solvents. It is also used in industrial chemicals and pollutants, including insecticides and other plastics.
Used in Environmental Estrogen Mimic Assessment:
Simazine is used in the assessment of environmental estrogen mimics, as it exhibits estrogen mimicry and shares common properties with other compounds that disrupt human health. It is used in various sensitive, rapid assays to detect and assess the activities of xenoestrogens by estrogen receptor proteins.
Used in Health Risk Assessment:
Simazine is considered in health risk assessment, as it is a potential endocrine disruptor compound (EDC) that can influence biological events occurring during ovulation, pregnancy, fetal development, and lactation. It is used in discussions regarding the relationships between assessment in vitro of xenoestrogen activities and their effects in vivo resulting in a risk to health.
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.
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
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.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Simazine is hydrolyzed by strong acids and alkalis .
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.
Fire Hazard
Literature sources indicate that Simazine is nonflammable.
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?
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.
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).
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.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 122-34-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 122-34:
(5*1)+(4*2)+(3*2)+(2*3)+(1*4)=29
29 % 10 = 9
So 122-34-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)
122-34-9Relevant academic research and scientific papers
Barton, Benita,Gouws, Shawn,Schaefer, Melissa C.,Zeelie, Bernard
, p. 1071 - 1076 (2003)
The sequence of reagent addition and associated heats of reaction during the synthesis of the important herbicide atrazine (6-chloro-N 2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine) from cyanuric chloride, isopropylamine, and ethylamine have been investigated by means of calorimetric and analytical methods. Sodium hydroxide was used as proton scavenger in this procedure. The best addition sequence found was the concurrent addition of amine and NaOH, keeping the amine in slight excess at all times. Using this feed sequence, the reaction becomes feed-controlled, and provided that a proper level of mixing can be maintained in the reactor, a high degree of control over reaction selectivity is obtained.
Design, synthesis, biological evaluation, and molecular docking study on triazine based derivatives as anti-inflammatory agents
Alvani, Mohsen,Asadi, Parvin,Hajhashemi, Valiollah,Khodarahmi, Ghadamali,Rostami, Mahboubeh
, (2021/07/01)
In an attempt to develop new anti-inflammatory agents, design, synthesis, pharmacological activities, and docking study of two groups of triazine-based derivatives were reported. Nine compounds (5a-5d and 10a-10e) consisting of triazine, vanillin, and phenylpyrazole were synthesized through the pharmacophore hybridization method. After confirmation of the structure of the synthesized compounds using spectroscopic methods (FT-IR, and NMR spectral data), their anti-inflammatory activity was evaluated using carrageenan-induced paw edema model in male Wistar rats (200–220 g) administered intraperitoneally at doses of 100 and 200 mg/kg. A group of rats received indomethacin (10 mg/kg) as the standard drug. Among compounds 5a to 5d, only compounds 5c and 5d showed a significant anti-inflammatory effect (p 0.01). Also compound 10a at a dose of (200 mg/kg) and compounds 10b, 10c, 10d and 10e at both doses showed significant anti-inflammatory activity and this effect for 10a (200 mg/kg) and both doses of 10b and 10e was comparable with indomethacin. While indomethacin reduced paw edema by 90%, 10b as the most potent tested compound reduced edema by 93%. The synthesized compounds were docked into the binding sites of both cyclooxygenase-1- and 2- isoenzymes (COX-1 and COX-2) to explore their binding mode and possible interactions of these ligands.
Continuous production method of multi-kettle serial triazine herbicide
-
Paragraph 0100; 0105-0109, (2019/05/04)
The invention relates to a continuous production method of a multi-kettle serial triazine herbicide. A metered cyanuric chloride solution is pre-cooled and mixed with alkylamine R1 in a mixer to entera first-stage reaction kettle, continuous discharging is conducted, after a heat exchanger is passed, the cyanuric chloride solution is neutralized with alkali in the mixer and enters a first-stage neutralization kettle, after a reaction is completed, the cyanuric chloride solution passes through a continuous water separator and the heat exchanger and is mixed with alkylamine R2 in the mixer to enter a second-stage reaction kettle, the continuous discharging is conducted, after the cyanuric chloride solution passes through the heat exchanger, the cyanuric chloride solution is mixed with the alkali in the mixer to enter a second-stage neutralization kettle, after the neutralization, a aqueous phase is separated by a continuous layerer, a solvent is removed, and drying is conducted to obtain a triazine product. The production method has the advantages of high productivity, good production stability, high efficiency, high product quality and the like, is particularly suitable for technical transformation of existing production enterprises, has a low transformation cost, basically does not add novel reaction equipment, and is easily mastered by existing enterprises.
Cardioprotective effect of novel sulphonamides-1,3,5-triazine conjugates against ischaemic–reperfusion injury via selective inhibition of MMP-9
Zheng, Xiao-Zhu,Zhou, Jia-Li,Ye, Jing,Guo, Pei-Pei,Lin, Chun-Shui
, p. 756 - 765 (2016/10/19)
Diseases affecting cardiovascular system are ranked as a top most cause of morbidity and mortality. Herein, a novel class sulphonamides-1,3,5-triazine conjugates have been synthesized and tested for inhibitory activity against MMP-2 and MMP-9. The results of the study showed that these molecules efficiently inhibit MMP-9 than MMP-2, revealing compound 8e as the most potent inhibitor (IC50?=?2.34?±?0.56?nm). Due to involvement of MMP-9 in many cardiovascular diseases, particularly in myocardial ischaemia (MI), compound 8e was further subjected for the determination of the protective effect on isoproterenol (ISO)-induced myocardial injury in rats.
NOVEL COMPOUNDS AS RESPIRATORY STIMULANTS FOR TREATMENT OF BREATHING CONTROL DISORDERS OR DISEASES
-
Page/Page column 62; 63, (2012/06/16)
The present invention includes compositions that are useful in the treatment of breathing control diseases or disorders in a subject in need thereof. The present invention also includes a method of treating a respiratory disease or disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutical formulation of the invention, The present invention further includes a method of preventing destabilization or stabilizing breathing rhythm in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutical formulation of the invention.
Chalcones, pyrazolines and aminopyrimidines as antibacterial agents
Solankee, Anjani,Lad, Smruti,Solankee, Sejal,Patel, Ghanshyam
experimental part, p. 1442 - 1446 (2010/03/30)
2,4-Bis-ethylamino-6-[4'-{3"-(substitutedphenyl/2'"-furanyl)-2' -propenone-l "-yl} phenyl amino]-s-triazine 5a-d have been prepared by treating ketone 4 with different substituted aromatic and heterocyclic aldehydes in the presence of alkali. These chalcones 5a-d on cyclisation with hydrazine hydrate and guanidine nitrate to form pyrazolines 6a-d and aminopyrimidines 7a-d respectively. The structures of the synthesized compounds have been established on the bases of IR,1H NMR and elemental analysis. The compounds have been evaluated for antibacterial activity against E. coli. S. paratyphi-A, S. aureus and B. subtilis.
Synthesis and biological evaluation of some new 3,4-dihydropyrimidin-4-ones
Modha, Jayesh,Datta, Neela,Parekh, Hansa
, p. 641 - 646 (2007/10/03)
Condensation of 5-cyano-2-hydrazino-3-N-methyl-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4 -one (3a and 3b) with 2,4-bisalkyl/arylamino-6-chloro-s-triazine (4) gave the corresponding 2,4-bisalkyl/arylamino-6-[5′-cyano-3′-N-methyl]-6′-phenyl/p -chlorophenyl-3′,4′-dihydropyrimidin-4′-one-2′-yl-hyd razino-s-triazines (5a-n and 6a-n). The compounds 4 have been prepared by the condensation of cyanuric chloride and different alkyl/aryl amines. The reaction between 5-cyano-3-N-methyl-2-methylthio-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin- 4-one (2a and 2b) with hydrazine hydrate furnished 3a and 3b, respectively. The condensation of 6-phenyl/p-chlorophenyl/5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one (1a and 1b) with methyl iodide yielded 2a and 2b, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv. Copyright
Herbicidal compositions comprising diamino-1,3,5-triazine and chloroacetanilide herbicides and a surfactant system
-
, (2008/06/13)
Flowable herbicidal compositions which contain an active component combination of at least one triazine and at least one chloroacetanilide with a surfactant component. This surfactant component, which consists of an anionic compound based on a monosulfuric acid ester of alkyl or alkyphenol polyglycol ethers as well as at least one nonionic alkyl or alkylphenol polyglycol ether, gives stable dispersions of the concentrated composition and forms stable dispersions of dilutions of the compositions suitable for direct use.
Halopyridyl triazolinone herbicides and herbicidal use thereof
-
, (2008/06/13)
Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.
5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides
-
, (2008/06/13)
5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.
