61-82-5 Usage
Chemical Properties
white powder or crystals
Uses
Different sources of media describe the Uses of 61-82-5 differently. You can refer to the following data:
1. Nonselective, 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
2. catalase inhibitor
3. Herbicide; plant regulator.
Definition
A 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.
Production Methods
3-Amino-1,2,4-Triazole（Amitrole） is synthesized by condensing formic acid with
aminoguanidine and can be purified by recrystallization
from methanol.
General Description
Odorless 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 Reactions
Water soluble. Aqueous solutions are neutral. Dust may form an explosive mixture in air.
Reactivity Profile
3-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 .
Hazard
Toxic; carcinogen.
Health Hazard
Amitrole (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 Hazard
Literature sources indicate that Triazol-3-amine is non-combustible.
Agricultural Uses
Herbicide, Plant growth regulator: 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.
Trade name
AMITRIL?; 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 Actions
BTK (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 Profile
Confirmed 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
Carcinogenicity
Amitrole is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Soil. 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 thistlSurface 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 biodegradationPhotolytic. 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
Purification Methods
It 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 61-82-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 1 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 61-82:
(4*6)+(3*1)+(2*8)+(1*2)=45
45 % 10 = 5
So 61-82-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H4N4/c3-6-2-1-4-5-6/h1-2H,3H2
61-82-5Relevant articles and documents
A 3D chiral metal-organic framework based on left-handed helices containing 3-amino-1 H-1,2,4-triazole ligand
Liu, Bing,Yang, Tian-Yi,Feng, Hui-Jun,Zhang, Zong-Hui,Xu, Ling
, p. 90 - 94 (2015)
A chiral metal-organic framework, [Cu(atr)(OH)]0.5H2O0.5en (1) (Hatr=3-amino-1 H-1,2,4-triazole, en=ethylenediamine), was constructed via diffusion reaction of the achiral Hatr ligand and CuSO4 as starting materials. Compound 1 crystallizes in the chiral space group P3221 and features a porous metal-organic framework with 44.1% solvent-accessible volume fabricated by left-handed helices with a pitch height of lp=10.442 ?. Six helices gather around in a cycle forming a large honeycomb channel with a 6.58 ? inner diameter. Cu(II) center and atr- ligand regarded as 3-connected nodes, compound 1 can be simplified to a 3-c uninodal {4.122} (qtz-h) topological network. A gradual decreasing in the magnetic moment depending on temperature decreasing indicates an antiferromagnetic interaction in 1. The powder XRD confirms the bulk sample is a single crystal pure phase, and the thermogravimetric analysis shows the thermal stability of 1 is up to ca. 240 °C.
Comparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors
Silveira, Flávia F.,de Souza, Juliana O.,Hoelz, Lucas V.B.,Campos, Vinícius R.,Jabor, Valquíria A.P.,Aguiar, Anna C.C.,Nonato, M. Cristina,Albuquerque, Magaly G.,Guido, Rafael V.C.,Boechat, Nubia,Pinheiro, Luiz C.S.
, (2020/11/10)
In this work, we designed and synthesized 35 new triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives as P. falciparum inhibitors (3D7 strain). Thirty compounds exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1 μM. The [1,2,4]triazolo[1,5-a]pyrimidine derivatives were more potent than the pyrazolo[1,5-a]pyrimidine and quinoline analogues. Compounds 20, 21, 23 and 24 were the most potent inhibitors, with IC50 values in the range of 0.030–0.086 μM and were equipotent to chloroquine. In addition, the compounds were selective, showing no cytotoxic activity against the human hepatoma cell line HepG2. All [1,2,4]triazolo[1,5-a]pyrimidine derivatives inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08–1.3 μM) and did not show significant inhibition against the HsDHODH homologue (0–30% at 50 μM). Molecular docking studies indicated the binding mode of [1,2,4]triazolo[1,5-a]pyrimidine derivatives to PfDHODH, and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro experimental evaluation. Thus, the most active compounds against P. falciparum parasites 20 (R = CF3, R1 = F; IC50 = 0.086 μM), 21 (R = CF3; R1 = CH3; IC50 = 0.032 μM), 23, (R = CF3, R1 = CF3; IC50 = 0.030 μM) and 24 (R = CF3, 2-naphthyl; IC50 = 0.050 μM) and the most active inhibitor against PfDHODH 19 (R = CF3, R1 = Cl; IC50 = 0.08 μM - PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggest that this is the mechanism of action underlying this series of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives.
Kinetics and mechanism of uncatalyzed and ruthenium(III)-catalyzed oxidation of formamidine derivative by hexacyanoferrate(III) in aqueous alkaline medium
FAWZY
, p. 733 - 743 (2016/05/19)
The catalytic effect of ruthenium(III) on the oxidation of N, N-dimethyl- N′-(4H-1,2,4-triazol- 3-yl) formamidine (ATF) by hexacyanoferrate(III) (HCF) was studied spectrophotometrically in aqueous alkaline medium. Both uncatalyzed and catalyzed reactions showed first order kinetics with respect to [HCF], whereas the reaction orders with respect to [ATF] and [OH ?] were apparently less than unity over the concentration range studied. A first order dependence with respect to [RuIII] was obtained. Increasing ionic strength increased the rate of uncatalyzed reaction and decreased the rate of the catalyzed one Plausible mechanistic schemes of oxidation reactions have been proposed. In both cases, the final oxidation products are identified as aminotriazole, dimethyl amine and carbon dioxide. The rate laws associated with the reaction mechanisms are derived. The reaction constants involved in the different steps of the mechanisms were calculated. The activation and thermodynamic parameters have been computed and discussed. [Figure not available: see fulltext.]
Kinetic and Mechanistic Aspects of Oxidation of Aminotriazole Formamidine by Cerium(IV) in Aqueous Perchloric and Sulfuric Acid Solutions: A Comparative Study
Fawzy, Ahmed
, p. 246 - 264 (2016/02/23)
The kinetics of the oxidation of an aminotriazole formamidine derivative, N,N-dimethyl-N′-(4H-1,2,4-triazol-3-yl) formamidine (ATF) by cerium(IV) has been studied spectrophotometrically in aqueous perchloric and sulfuric acid solutions at constant ionic strength of 1.0 mol·dm-3. In both acids, the reaction shows first order kinetics with respect to [Ce(IV)], whereas the orders with respect to [ATF] are less than unity. The reaction exhibits negative fractional order kinetics with respect to [H+]. The rates of reaction are not significantly affected by variations of either ionic strength or relative permittivity of the reaction's media. Addition of cerium(III) product does not affect the rates. Plausible mechanistic schemes for the reactions have been proposed. In both cases, the final oxidation products were identified as aminotriazole, dimethyl amine and carbon dioxide. Under comparable experimental conditions, the oxidation rate in perchloric acid solution is about sixfold higher than that in sulfuric acid solution. The effect of temperature on the rates has also been studied and activation parameters have been evaluated and discussed. The rate laws associated with the reaction mechanisms are derived.
