| 3-Amino-1,2,4-triazole[1] | |
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3-Amino-1,2,4-triazole |
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Other names
1,2,4-Triazol-3-amine |
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| Identifiers | |
| Abbreviations | 3-AT |
| CAS number | 61-82-5 |
| ChemSpider | 1577 |
| UNII | ZF80H5GXUF |
| EC number | 200-521-5 |
| KEGG | C11261 |
| ChEBI | CHEBI:40036 |
| ChEMBL | CHEMBL232801 |
| RTECS number | XZ3850000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H4N4 |
| Molar mass | 84.08 |
| Density | 1.138 g/mol |
| Melting point |
157 - 159 °C |
| Solubility in water | 280 gm/liter |
| Hazards | |
| R-phrases | R48/22 R51/53 R63 |
| S-phrases | (S2) S13 S36/37 S61 |
| Flash point | Nonflammable |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
3-Amino-1,2,4-triazole (3-AT) is a heterocyclic organic compound that consists of a 1,2,4-triazole substituted with an amino group.
3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase.[2] Imidazoleglycerol-phosphate dehydratase is an enzyme catalysing the sixth step of histidine production.[3]
3-AT is also is 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 [4] and approved by the European Parliament on January 13, 2009.[5]
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. Of course this selection process is performed using selective media, containing no histidine.
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 crop was tainted with traces of the herbicide aminotriazole [6]. The market for cranberries collapsed and growers lost millions of dollars.
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