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 organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

that consists of 1,2,4-triazole with an

amino group In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

as a

substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

. 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''. Exploits ...

gene, imidazoleglycerol-phosphate dehydratase. 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 Isomer, isomerism, depending on the positioning of the nitrogen atoms w ...

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

used on nonfood croplands to control

annual 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 (band), a ...

grasses and broadleaf and aquatic

weed A weed is a plant considered undesirable in a particular situation, growing where it conflicts with human preferences, needs, or goals.Harlan, J. R., & deWet, J. M. (1965). Some thoughts about weeds. ''Economic botany'', ''19''(1), 16-24. Pla ...

s. It is not used on

food Food is any substance consumed by an organism for Nutrient, nutritional support. Food is usually of plant, animal, or Fungus, fungal origin and contains essential nutrients such as carbohydrates, fats, protein (nutrient), proteins, vitamins, ...

crops A crop is a plant that can be grown and harvested extensively for profit or subsistence. In other words, a crop is a plant or plant product that is grown for a specific purpose such as food, fibre, or fuel. When plants of the same species a ...

because of its

carcinogenic A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and Biological agent, biologic agent ...

properties. As an herbicide, it is known as ''aminotriazole'', ''amitrole'' or ''amitrol''. Amitrol was included in a

biocide A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a sli ...

ban proposed by the

Swedish Chemicals Agency Swedish or ' may refer to: Anything from or related to Sweden, a country in Northern Europe. Or, specifically: * Swedish language, a North Germanic language spoken primarily in Sweden and Finland ** Swedish alphabet, the official alphabet used by ...

and approved by the European Parliament on January 13, 2009. Amitrol's mode of action is unknown, though it is classed as a

resistance group A resistance movement is an organized group of people that tries to resist or try to overthrow a government or an occupying power, causing disruption and unrest in civil order and stability. Such a movement may seek to achieve its goals through ei ...

Q herbicide.

Applications in microbiology

By applying 3-AT to a yeast

cell culture Cell culture or tissue culture is the process by which cell (biology), cells are grown under controlled conditions, generally outside of their natural environment. After cells of interest have been Cell isolation, isolated from living tissue, ...

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 Amine, α-amino group (which is in the protonated –NH3+ form under Physiological condition, biological conditions), a carboxylic ...

(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''. Differe ...

, containing no histidine.

1959 cranberry contamination

On November 9, 1959, the secretary of the

United States Department of Health, Education, and Welfare The United States Department of Health and Human Services (HHS) is a cabinet-level executive branch department of the US federal government created to protect the health of the US people and providing essential human services. Its motto is ...

, Arthur S. Flemming, announced that some of the 1959 cranberry 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 1959 incident.

References

{{DEFAULTSORT:Amino-1, 2, 4-Triazole, 3- Enzyme inhibitors Herbicides Endocrine disruptors Triazoles Cranberries Group 11 herbicides