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3-Amino-1,2,4-Triazole

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3-Amino-1,2,4-Triazole Basic information
Product Name:3-Amino-1,2,4-Triazole
Synonyms:Amino-s-triazole;AMINOTRIAZOLE;AMIZOLE;AMIZOL(R);AMITROL;AMITROLE;AMITROLE(R);amino-1,2,4-triazole
CAS:61-82-5
MF:C2H4N4
MW:84.08
EINECS:200-521-5
Product Categories:ATA;3-Amino-1,2,4-Triazole;Organic chemical, pesticide;AM to AQ;A;Alphabetic;Agro-Products;Estradiol, etc. (Environmental Endocrine Disruptors);Analytical Chemistry;Environmental Endocrine Disruptors;Heterocycles;Organics
Mol File:61-82-5.mol
3-Amino-1,2,4-Triazole Structure
3-Amino-1,2,4-Triazole Chemical Properties
Melting point 150-153 °C(lit.)
Boiling point 144.35°C (rough estimate)
bulk density650kg/m3
density 1.138
vapor pressure <0.1 hPa (20 °C)
refractive index 1.6260 (estimate)
storage temp. Store below +30°C.
solubility 280g/l
pka11.14±0.20(Predicted)
form Powder or Flakes
color White to off-white or yellow
PH6.4-7.4 (100g/l, H2O, 20℃)
biological sourcesynthetic (organic)
Water Solubility 280 g/L (20 ºC)
Merck 14,489
BRN 107687
Specific Activity37-49nmol/min·mg
Exposure limitsNIOSH REL: TWA 0.2 mg/m3; ACGIH TLV: TWA 0.2 mg/m3.
Stability:Stable. Incompatible with iron, copper, aluminium, acids, alkalies, strong oxidizing agents, acid chlorides, acid anhydrides. Forms chelates with some metals. Moisture sensitive.
InChI1S/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
InChIKeyKLSJWNVTNUYHDU-UHFFFAOYSA-N
SMILESNc1nc[nH]n1
LogP-0.860
CAS DataBase Reference61-82-5(CAS DataBase Reference)
IARC3 (Vol. 79, Sup 7) 2001
NIST Chemistry Reference3-Amino-s-triazole(61-82-5)
EPA Substance Registry SystemAmitrole (61-82-5)
Safety Information
Hazard Codes Xn,N,T
Risk Statements 48/22-51/53-63-40-61
Safety Statements 13-36/37-61-45-53
OEBC
OELTWA: 0.2 mg/m3
RIDADR UN 3077 9/PG 3
WGK Germany 2
RTECS XZ3850000
Autoignition Temperature>225 °C
TSCA TSCA listed
HazardClass 9
PackingGroup III
HS Code 29339990
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Chronic 2
Repr. 2
STOT RE 2
Hazardous Substances Data61-82-5(Hazardous Substances Data)
ToxicityLD50 in mice, rats (g/kg): 14.7, 25.0 orally (Krller)
MSDS Information
ProviderLanguage
Amino-s-triazole English
SigmaAldrich English
ACROS English
ALFA English
3-Amino-1,2,4-Triazole Usage And Synthesis
Chemical Properties3-Amino-1,2,4-triazole, also known as amitrole, is a colorless to off-white crystalline solid or white powder. It is odorless when pure and is soluble in water, methanol, ethanol, and chloroform, but insoluble in diethyl ether and acetone.
Usescatalase inhibitor
UsesNonselective, foliage-applied, systemic, triazole herbicide used in uncropped land and orchards to control certain grasses and to kill annual and perennial grasses and weeds. It is also effective on poison ivy, poison oak and aquatic weeds
Production Methods3-Amino-1,2,4-Triazole(Amitrole) is synthesized by condensing formic acid with aminoguanidine and can be purified by recrystallization from methanol.
DefinitionA powerful plant growth suppressant and cotton defoliant that is readily absorbed by leaves and roots. 3-Amino-1,2,4-Triazole inhibits many aspects of growth and differentiation including cell division in the primary root meristems in some plants.
General DescriptionOdorless white crystals or white powder. Bitter taste. Melting point 147-159°C. Sublimes undecomposed at reduced pressure. Used as a post-emergence herbicide.
Air & Water ReactionsWater soluble. Aqueous solutions are neutral. Dust may form an explosive mixture in air.
Reactivity Profile3-Amino-1,2,4-Triazole is a triazole derivative. The triazoles are a group that contain several derivatives that are highly explosive materials. They are sensitive to heat, friction, and impact. Sensitivity varies with the type substitution to the triazole ring. Metal chelated and halogen substitution of the triazol ring make for a particularly heat sensitive material. Azido and nitro derivatives have been employed as high explosives. No matter the derivative these materials should be treated as explosives. It forms chelates with some metals. 3-Amino-1,2,4-Triazole is corrosive to iron, copper and aluminum. Forms salts with most acids and alkalis. It is incompatible with strong oxidizers, strong acids, acid chlorides and acid anhydrides .
HazardToxic; carcinogen.
Health HazardAmitrole (3-Amino-1,2,4-Triazole) has low acute toxicity; in experimental animal studies subchronic exposures were associated with changes in the thyroid and chronic exposures were carcinogenic.
Intentional ingestion of a mixture that contained 20 mg/kg amitrole did not cause any signs of intoxication.1 In one reported case study, inhalation of a large amount of amitrolecontaining herbicide was associated with acute toxic reaction of the lungs.2 Lung injury was thought to be secondary to direct toxic damage to the alveolar lining cells. The remarkable lack of any other reports describing pulmonary toxicity of this herbicide was noted, in addition to the presence of other chemicals in the herbicide solution.
Fire HazardLiterature sources indicate that Triazol-3-amine is non-combustible.
Agricultural Uses3-Amino-1,2,4-triazole is a non-food use herbicide for control of grasses, woody plants and broad-leaf weeds on hard surface and in areas where crops are not normally grown. It enters plant circulation through roots and is majorly present in the meristem. 3-Amino-1,2,4-triazole inhibits chlorophyll synthesis resulting in chlorotic leaves and albino plants. In addition, it also affects the growth of the plants. It is exploited to destroy unwanted weeds.
Trade nameAMITRIL®; ATLAZIN®; ATLAZINE® FLOWABLE; AT®; 3-AT®; AT-90®; ATRAFLOW PLUS®; AZAPLANT®; AZAPLANT KOMBI®; AZOLAN®; AZOLE®; BOROFLOW® A/ATA; CAMPAPRIM® A 1544; CDA SIMFLOW PLUS®; CHIPMAN® PATH; CYTROLE®; DIUROL® AMITROLE; DOMATOL®; ELMASIL®; EMISOL®; FARMCO®; HERBAZIN PLUS SC®; HERBICIDE® TOTAL; MASCOT HIGHWAY®; MSS AMINOTRIAZOLE®; MSS SIMAZINE®; ORGA-414®; RADOXONE® TL; RAMIZOL®; RASSAPRON®; SIMAZOL®; SIMFLOW PLUS®; SOLUTION CNCENTREE T271®; SYNCHEMICALS® TOTAL WEED KILLER; SYNTOX®; TORAPRON®; VOROX®; WEEDAR®; WEEDAZIN®; WEEDAZOL TL ®; WEEDOCLOR®
Biochem/physiol ActionsBTK (also known as Bruton tyrosine kinase) plays a crucial role in B-lymphocyte differentiation and activation. BTK interacts with SRC homology 3 domains of FYN, LYN and HCK that are activated upon stimulation of B- and T-cell receptors.Defects in the BTK gene cause Agammaglobulinemia, an X-linked immunodeficiency characterized by failure to produce mature B lymphocyte cells and associated with a failure of Ig heavy chain rearrangement. The unique role of BTK makes it a desirable target for potential anti-cancer, anti-inflammatory and anti-viral agents as well as other treatments.
Safety ProfileConfirmed carcinogen with experimental carcinogenic, tumorigenic, and neoplastigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,. An herbicide and plant growth regulator
Potential ExposureA potential danger to those involved in the manufacture, formulation, and application of this postemergence herbicide, which is now limited to noncrop applications as a herbicide and plant growth regulator. Some triazoles have been used as rubber components.
CarcinogenicityAmitrole is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental FateSoil. When radiolabeled amitrole-5-14C was incubated in a Hagerstown silty clay loam, 50 and 70% of the applied amount evolved as 14CO2 after 3 and 20 days, respectively. In autoclaved soil, however, no 14CO2 was detected. The chemical degradation in soil was probably via hydroxyl radicals (Kaufman et al., 1968). The average persistence in soils is 2–4 weeks (Hartley and Kidd, 1987)
Plant.Amitrole is transformed in plants to form the conjugate β-(3-amino-1,2,4-triazol- 1-yl)-α-alanine (Humburg et al., 1989) and/or 3-(3-amino-s-triazole-1-yl)-2-aminopropionic acid (Duke et al., 1991). Amitrole is metabolized in Canada thistl
Surface Water. In pond water, adsorption to suspended sediments was an important process. The initial half-life was reported to be no more than 68 days. After 120 days, 20% of the applied amount remained (Grzenda et al., 1966). The biodegradation
Photolytic. Direct photolysis of amitrole is not expected to occur since the herbicide shows little or no absorption greater than 295 nm (Gore et al., 1971)
Chemical/Physical. Reacts with acids and bases forming soluble salts (Hartley and Kidd, 1987). Emits toxic fumes of nitrogen oxides when heated to decomposition (Sax and Lewis, 1987); however, incineration with polyethylene results in more than 9
ShippingUN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification MethodsIt crystallises from EtOH (charcoal), then three times from dioxane [Williams et al. J Phys Chem 61 261 1957]. [Beilstein 26 H 137.] Possible carcinogen. [Beilstein 26 H 137, Temple & Montgomery 1,2,4-Triazoles —The Chemistry of Heterocyclic Compounds Vol 37 (Weissberger & Taylor eds.). Wiley & Sons NY 1981, ISBN 0-471-0656-6.]
IncompatibilitiesDust may be explosive in air. Keep away from strong oxidizers; strong acids; light and heat (decomposes). Corrosive to iron, aluminum, and copper. Sublimes undecomposed at reduced pressure.
Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Amitrol is resistant to hydrolysis and the action of oxidizing agents. Burning the compound with polyethylene is reported to result in .99% decomposition.
References[1] SERGEY M. DESENKO. Cyclecondensation of 3-amino-1,2,4-triazole with substituted methyl cinnamates[J]. Journal of Heterocyclic Chemistry, 2009, 36 1: 205-208. DOI:10.1002/jhet.5570360131
[2] XIAOTAO LIU . 3-Amino-1,2,4-triazole-derived graphitic carbon nitride for photodynamic therapy[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2021, 250: Article 119363. DOI:10.1016/j.saa.2020.119363.
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