3-Amino-1,2,4-triazole

Last updated
3-Amino-1,2,4-triazole [1]
Aminotriazole.png
Names
IUPAC name
1H-1,2,4-Triazol-3-amine
Other names
1,2,4-Triazol-3-amine
aminotriazole
Amitrol
Amitrole
3-Aminotriazole
2-Amino-1,3,4-triazole
Identifiers
3D model (JSmol)
Abbreviations3-AT
107687
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.474 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-521-5
200706
KEGG
MeSH Amitrole
PubChem CID
RTECS number
  • XZ3850000
UNII
  • InChI=1S/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6) Yes check.svgY
    Key: KLSJWNVTNUYHDU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
    Key: KLSJWNVTNUYHDU-UHFFFAOYAV
  • n1c[nH]nc1N
Properties
C2H4N4
Molar mass 84.082 g·mol−1
Appearancecolorless/white crystals or powder [2]
Odor odorless
Density 1.138 g/mL
Melting point 157 to 159 °C (315 to 318 °F; 430 to 432 K)
Boiling point 347
28 g/100 mL
Solubility soluble in acetonitrile, chloroform, ethanol, methanol, methylene chloride
negligible in ethyl acetate
Vapor pressure 3.13x10−9 mmHg
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
potential occupational carcinogen
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H361, H373, H411
P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
1,100 to 2,500 mg/kg
NIOSH (US health exposure limits):
PEL (Permissible)
none [2]
REL (Recommended)
Ca TWA 0.2 mg/m3 [2]
IDLH (Immediate danger)
Ca/N.D. [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

3-Amino-1,2,4-triazole (3-AT) is a heterocyclic organic compound that consists of 1,2,4-triazole with an amino group as a substituent.

Contents

3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase. [3] [4] Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production. [5]

3-AT is also a nonselective systemic triazole herbicide used on nonfood croplands to control annual grasses and broadleaf and aquatic weeds. It is not used on food crops because of its carcinogenic properties. As an herbicide, it is known as aminotriazole, amitrole or amitrol.

Amitrol was included in a biocide ban proposed by the Swedish Chemicals Agency [6] and approved by the European Parliament on January 13, 2009. [7] Amitrol's mode of action is unknown, though it is classed as a resistance group Q herbicide. [8]

Applications in microbiology

By applying 3-AT to a yeast cell culture which is dependent upon a plasmid containing HIS3 to produce histidine (i.e. its own HIS3 analogue is not present or nonfunctional), an increased level of HIS3 expression is required in order for the yeast cell to survive. This has proved useful in various two-hybrid system, where a high-affinity binding between two proteins (i.e., higher expression of the HIS3 gene) will allow the yeast cell to survive in media containing higher concentrations of 3-AT. This selection process is performed using selective media, containing no histidine.

1959 cranberry contamination

On November 9, 1959, the secretary of the United States Department of Health, Education, and Welfare, Arthur S. Flemming, announced that some of the 1959 cranberry crop was tainted with traces of the herbicide aminotriazole. [9] The market for cranberries collapsed and growers lost millions of dollars. [10] However, Ocean Spray recovered by expanding the market for cranberry juice, which, although widely available for sale, was before then not popular. This ensured cranberry growers would not have to rely mostly on Thanksgiving and Christmas for sales, which was the case until the 1959 incident.

Related Research Articles

<span class="mw-page-title-main">Protein kinase</span> Enzyme that adds phosphate groups to other proteins

A protein kinase is a kinase which selectively modifies other proteins by covalently adding phosphates to them (phosphorylation) as opposed to kinases which modify lipids, carbohydrates, or other molecules. Phosphorylation usually results in a functional change of the target protein (substrate) by changing enzyme activity, cellular location, or association with other proteins. The human genome contains about 500 protein kinase genes and they constitute about 2% of all human genes. There are two main types of protein kinase. The great majority are serine/threonine kinases, which phosphorylate the hydroxyl groups of serines and threonines in their targets. Most of the others are tyrosine kinases, although additional types exist. Protein kinases are also found in bacteria and plants. Up to 30% of all human proteins may be modified by kinase activity, and kinases are known to regulate the majority of cellular pathways, especially those involved in signal transduction.

<span class="mw-page-title-main">Phosphorylation</span> Chemical process of introducing a phosphate

In biochemistry, phosphorylation is the attachment of a phosphate group to a molecule or an ion. This process and its inverse, dephosphorylation, are common in biology. Protein phosphorylation often activates many enzymes.

<span class="mw-page-title-main">Histidine</span> Chemical compound

Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC.

<span class="mw-page-title-main">Auxotrophy</span> Inability to synthesize an organic compound required for growth

Auxotrophy is the inability of an organism to synthesize a particular organic compound required for its growth. An auxotroph is an organism that displays this characteristic; auxotrophic is the corresponding adjective. Auxotrophy is the opposite of prototrophy, which is characterized by the ability to synthesize all the compounds needed for growth.

<span class="mw-page-title-main">Pyridoxal phosphate</span> Active form of vitamin B6

Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions. The International Union of Biochemistry and Molecular Biology has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities. The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.

<span class="mw-page-title-main">Two-hybrid screening</span> Molecular biology technique

Two-hybrid screening is a molecular biology technique used to discover protein–protein interactions (PPIs) and protein–DNA interactions by testing for physical interactions between two proteins or a single protein and a DNA molecule, respectively.

A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring.

<span class="mw-page-title-main">Histidine decarboxylase</span> Enzyme that converts histidine to histamine

The enzyme histidine decarboxylase is transcribed on chromosome 15, region q21.1-21.2, and catalyzes the decarboxylation of histidine to form histamine. In mammals, histamine is an important biogenic amine with regulatory roles in neurotransmission, gastric acid secretion and immune response. Histidine decarboxylase is the sole member of the histamine synthesis pathway, producing histamine in a one-step reaction. Histamine cannot be generated by any other known enzyme. HDC is therefore the primary source of histamine in most mammals and eukaryotes. The enzyme employs a pyridoxal 5'-phosphate (PLP) cofactor, in similarity to many amino acid decarboxylases. Eukaryotes, as well as gram-negative bacteria share a common HDC, while gram-positive bacteria employ an evolutionarily unrelated pyruvoyl-dependent HDC. In humans, histidine decarboxylase is encoded by the HDC gene.

<span class="mw-page-title-main">Amino acid synthesis</span> The set of biochemical processes by which amino acids are produced

Amino acid biosynthesis is the set of biochemical processes by which the amino acids are produced. The substrates for these processes are various compounds in the organism's diet or growth media. Not all organisms are able to synthesize all amino acids. For example, humans can synthesize 11 of the 20 standard amino acids. These 11 are called the non-essential amino acids.

The HIS3 gene, found in the Saccharomyces cerevisiae yeast, encodes a protein called Imidazoleglycerol-phosphate dehydratase which catalyses the sixth step in histidine biosynthesis. It is analogous to hisB in Escherichia coli.

The hisB gene, found in the enterobacteria, in Campylobacter jejuni and in Xylella/Xanthomonas encodes a protein involved in catalysis of two step in histidine biosynthesis, namely the bifunctional Imidazoleglycerol-phosphate dehydratase/histidinol-phosphatase.

HIS-selective medium is a type cell culture medium that lacks the amino acid histidine. It can be used with bacteria reliant on the expression of a gene encoding proteins involved in histidine expression in order to survive. Only bacteria expressing such genes will survive on these media.

<span class="mw-page-title-main">3-dehydroquinate dehydratase</span> Class of enzymes

The enzyme 3-dehydroquinate dehydratase (EC 4.2.1.10) catalyzes the chemical reaction

<span class="mw-page-title-main">Imidazoleglycerol-phosphate dehydratase</span>

The enzyme imidazoleglycerol-phosphate dehydratase (EC 4.2.1.19) catalyzes the chemical reaction

<span class="mw-page-title-main">Two-component regulatory system</span> Method of stimulus sensing and response in cells

In molecular biology, a two-component regulatory system serves as a basic stimulus-response coupling mechanism to allow organisms to sense and respond to changes in many different environmental conditions. Two-component systems typically consist of a membrane-bound histidine kinase that senses a specific environmental stimulus, and a corresponding response regulator that mediates the cellular response, mostly through differential expression of target genes. Although two-component signaling systems are found in all domains of life, they are most common by far in bacteria, particularly in Gram-negative and cyanobacteria; both histidine kinases and response regulators are among the largest gene families in bacteria. They are much less common in archaea and eukaryotes; although they do appear in yeasts, filamentous fungi, and slime molds, and are common in plants, two-component systems have been described as "conspicuously absent" from animals.

<span class="mw-page-title-main">Bacterial one-hybrid system</span> Method for identifying the sequence-specific target site of a DNA-binding domain

The bacterial one-hybrid (B1H) system is a method for identifying the sequence-specific target site of a DNA-binding domain. In this system, a given transcription factor (TF) is expressed as a fusion to a subunit of RNA polymerase. In parallel, a library of randomized oligonucleotides representing potential TF target sequences are cloned into a separate vector containing the selectable genes HIS3 and URA3. If the DNA-binding domain (bait) binds a potential DNA target site (prey) in vivo, it will recruit RNA polymerase to the promoter and activate transcription of the reporter genes in that clone. The two reporter genes, HIS3 and URA3, allow for positive and negative selections, respectively. At the end of the process, positive clones are sequenced and examined with motif-finding tools in order to resolve the favoured DNA target sequence.

<span class="mw-page-title-main">EPSP synthase</span> Enzyme produced by plants and microorganisms

5-enolpyruvylshikimate-3-phosphate (EPSP) synthase is an enzyme produced by plants and microorganisms. EPSPS catalyzes the chemical reaction:

<span class="mw-page-title-main">Metribuzin</span> Chemical compound

Metribuzin is a herbicide used both pre- and post-emergence in crops including soy bean, potatoes, tomatoes and sugar cane.

Early twenty-first century pesticide research has focused on developing molecules that combine low use rates and that are more selective, safer, resistance-breaking and cost-effective. Obstacles include increasing pesticide resistance and an increasingly stringent regulatory environment.

<span class="mw-page-title-main">C21orf58</span> Protein-coding gene in the species Homo sapiens

Chromosome 21 Open Reading Frame 58 (C21orf58) is a protein that in humans is encoded by the C21orf58 gene.

References

  1. EXTOXNET – Herbicide fact sheet for amitrole
  2. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0027". National Institute for Occupational Safety and Health (NIOSH).
  3. Brennan MB, Struhl K (1980). "Mechanisms of increasing expression of a yeast gene in Escherichia coli". J. Mol. Biol. 136 (3): 333–8. doi:10.1016/0022-2836(80)90377-0. PMID   6990004.
  4. Joung JK, Ramm EI, Pabo CO (2000). "A bacterial two-hybrid selection system for studying protein-DNA and protein-protein interactions". Proc. Natl. Acad. Sci. U.S.A. 97 (13): 7382–7. Bibcode:2000PNAS...97.7382J. doi: 10.1073/pnas.110149297 . PMC   16554 . PMID   10852947.
  5. "Yeastgenome.org". Archived from the original on 2006-05-05. Retrieved 2006-12-01.
  6. "Interpretation of criteria for approval of active substances in the proposed EU plant protection regulation". Swedish Chemicals Agency (KemI). 2008-09-23. Archived from the original on 1 January 2009. Retrieved 2009-01-14.
  7. "MEPs approve pesticides legislation". 2009-01-13. Archived from the original on 25 January 2009. Retrieved 2009-01-14.
  8. "Australia Herbicide Classification Lookup". Herbicide Resistance Action Committee.
  9. "Safe Cranberries to Go on Sale". Dubuque Telegraph-Herald. 19 November 1959. Retrieved 10 February 2012.
  10. New York Times website - Opinion section