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Name |
Simazine |
EINECS | 204-535-2 |
CAS No. | 122-34-9 | Density | 1.302 g/cm3 |
PSA | 62.73000 | LogP | 1.53460 |
Solubility | 0.0005 g/100 mL in water | Melting Point |
225 °C |
Formula | C7H12ClN5 | Boiling Point | 365.8 °C at 760 mmHg |
Molecular Weight | 201.659 | Flash Point | 175 °C |
Transport Information | UN 2811 | Appearance | White powder |
Safety | 36/37-46-60-61-45 | Risk Codes | 40-50/53-39/23/24/25-23/24/25-11 |
Molecular Structure | Hazard Symbols | Xn,N | |
Synonyms |
1,3,5-Triazine-2,4-diamine,6-chloro-N,N'-diethyl- (9CI);2,4-Bis(ethylamino)-6-chloro-s-triazine;2,4-Di(ethylamino)-6-chloro-1,3,5-triazine;2-Chloro-4,6-bis(ethylamino)-s-triazine;2-Chloro-4,6-di(ethylamino)triazine;Aktinit S;Aquazine;Azotop;BatazinaFLO;Bitemol S 50;CAT;CAT (pesticide);CET;Geigy 27692;Gesatop D;H 1803;Herbatoxol S;Herbazin;Herbazin 50;Herbex;Hungazin DT;Radocon;Simanex;Simatox;Simatsin-neste;Simazin;Tafazine;Tafazine 50W;Triazine A 384;W 6658;Yrodazin; |
Article Data | 23 |
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 0 - 50℃; for 1.5h; | 92% |
With sodium carbonate In water; acetone at 0 - 20℃; | 81% |
With sodium hydrogencarbonate In acetone at 20℃; for 4h; pH=7; | 70% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 25 - 40℃; |
Conditions | Yield |
---|---|
With water; sodium carbonate for 1.5h; Heating; | 95% |
Simazine
carbonic acid dimethyl ester
2,4-Bis(ethylamino)-6-methylthio-1,3,5-triazine
Conditions | Yield |
---|---|
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; | 93% |
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 140℃; for 0.5h; | 85.5% |
In water; N,N-dimethyl-formamide at 130 - 135℃; for 0.5h; | 40% |
Simazine
2-ethoxy-ethanol
2,4-Bisethylamino-6-(2-ethoxy-ethoxy)-1,3,5-triazin
Conditions | Yield |
---|---|
With disodium cyanamide In water for 1.5h; Heating; | 82.5% |
Simazine
4-Aminoacetophenone
2,4-bis(ethylamino)-6-(4'-acetylphenylamino)-1,3,5-triazine
Conditions | Yield |
---|---|
With sodium carbonate In water; N,N-dimethyl-formamide for 12h; Reflux; | 78% |
Simazine
Diethyl carbonate
N2,N4-diethyl-6-(ethylthio)-1,3,5-triazine-2,4-diamine
Conditions | Yield |
---|---|
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere; | 76% |
Simazine
p-aminoethylbenzoate
ethyl(2,4-bis-ethylamino-s-triazin-6-yl)aminobenzoate
Conditions | Yield |
---|---|
In 1,4-dioxane for 2h; Heating; | 73% |
Simazine
ethanolamine
2-(4,6-Bis-ethylamino-[1,3,5]triazin-2-ylamino)-ethanol
Conditions | Yield |
---|---|
With sodium methylate | 70% |
Molecule structure of Simazine (CAS NO.122-34-9):
IUPAC Name: 6-chloro-2-N,4-N-diethyl-1,3,5-triazine-2,4-diamine
Molecular Weight: 201.65668 g/mol
Molecular Formula: C7H12ClN5
Density: 1.318 g/cm3
Boiling Point: 365.8 °C at 760 mmHg
Flash Point: 175 °C
Index of Refraction: 1.622
Molar Refractivity: 53.9 cm3
Molar Volume: 152.9 cm3
Polarizability: 21.37×10-24 cm3
Surface Tension: 58.4 dyne/cm
Enthalpy of Vaporization: 61.21 kJ/mol
Vapour Pressure: 1.53E-05 mmHg at 25 °C
XLogP3: 2.2
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Tautomer Count: 5
Exact Mass: 201.078123
MonoIsotopic Mass: 201.078123
Topological Polar Surface Area: 62.7
Heavy Atom Count: 13
Complexity: 131
Canonical SMILES: CCNC1=NC(=NC(=N1)Cl)NCC
InChI: InChI=1S/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)
InChIKey: ODCWYMIRDDJXKW-UHFFFAOYSA-N
Simazine (CAS NO.122-34-9) can be widely used as a residual non-selective herbicide. In European Union states (EU directive 91/414/EEC), it is banned . It acts by inhibiting photosynthesis like atrazine. After application, It remains active in the soil for 2-7 months.
Simazine can be prepared in the laboratory from cyanuric chloride crystals and a strong solution of ethyl amine which is at least 50 percent by number in water. The reaction is highly exothermic and is therefore best carried out in an ice bath below 10 °C. It is also essential to carry out the synthesis in a fume hood since cyanuric chloride decomposes at high temperatures into hydrogen chloride and hydrogen cyanide both of which are highly toxic by inhalation.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | > 5gm/kg (5000mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984, | |
mammal (species unspecified) | LD50 | oral | 2014mg/kg (2014mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | National Technical Information Service. Vol. PB288-416, |
mammal (species unspecified) | LD50 | unreported | 1400mg/kg (1400mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(6), Pg. 81, 1979. | |
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04003, | |
mouse | LDLo | oral | 5gm/kg (5000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 27(8), Pg. 22, 1962. |
pigeon | LD50 | oral | > 5gm/kg (5000mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984, | |
rabbit | LD50 | oral | > 5gm/kg (5000mg/kg) | "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984, | |
rabbit | LD50 | skin | > 10200mg/kg (10200mg/kg) | Yakkyoku. Pharmacy. Vol. 37, Pg. 427, 1986. | |
rat | LC50 | inhalation | 9800mg/m3/4H (9800mg/m3) | Farm Chemicals Handbook. Vol. -, Pg. C275, 1991. | |
rat | LD50 | oral | 971mg/kg (971mg/kg) | Fundamental and Applied Toxicology. Vol. 7, Pg. 299, 1986. | |
rat | LD50 | skin | > 5gm/kg (5000mg/kg) | Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 315, 1990. | |
rat | LD50 | unreported | 1390mg/kg (1390mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 7(5), Pg. 54, 1963. |
Simazine (CAS NO.122-34-9) is an off-white crystalline compound which is sparingly soluble in water. Simazine (CAS NO.122-34-9) is also called 1-Chloro-3,5-bis(ethylamino)-2,4,6-triazine ; 2,4-Bis(aethylamino)-6-chlor-1,3,5-triazin ;
2,4-Bis(aethylamino)-6-chlor-1,3,5-triazin [German] ; 2,4-Bis(ethylamino)-6-chloro-s-triazine ; 2-Chloro-4,6-bis(ethylamino)-1,3,5-triazine ; 2-Chloro-4,6-bis(ethylamino)-s-triazine ; 4-26-00-01208 (Beilstein Handbook Reference) ; 6-Chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine ; 6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine ; A 2079 ; AI3-51142 ; Aktinit S ; Amizine ; Aquazine ; Azotop ; BRN 0010895 ; Batazina ; Batazine FLO ; Bitemol ; Bitemol S 50 ; CAT ; CAT (herbicide) ; CCRIS 1469 ; CDT ; CET ; Caswell No. 740 ; Cekusan ; Cekusima ; Cekuzina-S ; EPA Pesticide ; Chemical Code 080807 ; G 27692 ; G-27692 ; Geigy 27,692 ; Gesapun ; Gesaran ; Gesatop ; Gesatop 50 ; H 1803 ; HSDB 1765 ; Herbatoxol S ; Herbazin ; Primatel S ; Primatol S ; Princep ; Simanex ; Simatsin-neste ; Simazine 80W ; Symazine ; Tafazine ; Tafazine (VAN) ; Tafazine 50-W ; Taphazine ; Triazine A 384 ; W 6658 ; Yrodazin ; Zeapur .