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3-Amino-1,2,4-triazole



3-Amino-1,2,4-triazole[1]
IUPAC name 3-Amino-1,2,4-triazole
Other names 1,2,4-Triazol-3-amine
aminotriazole
Amitrol
Amitrole
Identifiers
Abbreviations 3-AT
CAS number 61-82-5
EINECS number 200-521-5
RTECS number XZ3850000
SMILES NC1=NNC=N1
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
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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.

Additional recommended knowledge

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.

Exploits

By applying 3-AT to a bacterial 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 bacterial cell to survive. This has proved useful in increasing the affinity of DNA-binding domains selected in one bacterial two-hybrid technique described by Joung et al., in 2000. Since the DNA-binding domain in turn recruits RNA polymerase to the HIS3 gene, a high affinity binding will allow the bacterial cell to survive in media containing higher concentrations of 3-AT. Of course 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 crop was tainted with traces of the herbicide aminotriazole [4]. The market for cranberries collapsed and growers lost millions of dollars.

References

  1. ^ EXTOXNET - Herbicide fact sheet for amitrole
  2. ^ Joung, J. K., E. I. Ramm and C. O. Pabo (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.
  3. ^ Yeastgenome.org
  4. ^ New York Times website - Opinion section
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "3-Amino-1,2,4-triazole". A list of authors is available in Wikipedia.
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