3-Amino-1,2,4-triazole (3-AT) is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

that consists of a

1,2,4-triazole 1,2,4-Triazole (as ligand in coordination compounds, Htrz abbreviation is sometimes used) is one of a pair of isomeric chemical compounds with molecular formula CHN, called triazoles, which have a five-membered ring of two carbon atoms and three n ...

substituted with an

amino group In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

. 3-AT is a competitive inhibitor of the product of the

HIS3 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''. Exploi ...

gene,

imidazoleglycerol-phosphate dehydratase The enzyme imidazoleglycerol-phosphate dehydratase () catalyzes the chemical reaction :D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate \rightleftharpoons 3-(imidazol-4-yl)-2-oxopropyl phosphate + H2O This enzyme belongs to the family of lyases ...

. Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production. 3-AT is also a nonselective systemic

triazole 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 t ...

herbicide used on nonfood

cropland Agricultural land is typically land ''devoted to'' agriculture, the systematic and controlled use of other forms of lifeparticularly the rearing of livestock and production of cropsto produce food for humans. It is generally synonymous with bot ...

s to control

annual grass Annual may refer to: * Annual publication, periodical publications appearing regularly once per year **Yearbook ** Literary annual * Annual plant * Annual report * Annual giving * Annual, Morocco, a settlement in northeastern Morocco * Annuals (b ...

es and broadleaf and aquatic

weed A weed is a plant considered undesirable in a particular situation, "a plant in the wrong place", or a plant growing where it is not wanted.Harlan, J. R., & deWet, J. M. (1965). Some thoughts about weeds. ''Economic botany'', ''19''(1), 16-24. ...

s. It is not used on food crops because of its

carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

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 and approved by the European Parliament on January 13, 2009.

Applications in microbiology

By applying 3-AT to a yeast cell culture which is dependent upon a plasmid containing HIS3 to produce

histidine 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 d ...

(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 A growth medium or culture medium is a solid, liquid, or semi-solid designed to support the growth of a population of microorganisms or cells via the process of cell proliferation or small plants like the moss ''Physcomitrella patens''. Different ...

, 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 Arthur Sherwood Flemming (June 12, 1905September 7, 1996) was an American government official. He served as the United States Secretary of Health, Education, and Welfare from 1958 until 1961 under President Dwight D. Eisenhower's administration ...

announced that some of the 1959 crop was tainted with traces of the herbicide aminotriazole. The market for cranberries collapsed and growers lost millions of dollars.New York Times website - Opinion section
/ref> 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 notorious 1959 incident.

References

{{DEFAULTSORT:Amino-1, 2, 4-Triazole, 3- Enzyme inhibitors Herbicides Endocrine disruptors Triazoles Cranberries