1-Naphthaleneacetic acid (NAA) is an

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. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

C₁₀H₇CH₂CO₂H. This colorless solid is soluble in organic solvents. It features a carboxylmethyl group (CH₂CO₂H) linked to the "1-position" of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

Use and regulation

NAA is a synthetic

plant hormone Plant hormone (or phytohormones) are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, from embryogenesis, the regulation of organ size, pa ...

in the

auxin Auxins (plural of auxin ) are a class of plant hormones (or plant-growth regulators) with some morphogen-like characteristics. Auxins play a cardinal role in coordination of many growth and behavioral processes in plant life cycles and are essenti ...

family and is an ingredient in many commercial plant rooting

horticultural Horticulture is the branch of agriculture that deals with the art, science, technology, and business of plant cultivation. It includes the cultivation of fruits, vegetables, nuts, seeds, herbs, sprouts, mushrooms, algae, flowers, seaweeds and no ...

products; it is a rooting agent and used for the

vegetative propagation Vegetative reproduction (also known as vegetative propagation, vegetative multiplication or cloning) is any form of asexual reproduction occurring in plants in which a new plant grows from a fragment or cutting of the parent plant or speci ...

of plants from stem and leaf cuttings. It is also used for

plant tissue culture Plant tissue culture is a collection of techniques used to maintain or grow plant cells, tissues or organs under sterile conditions on a nutrient culture medium of known composition. It is widely used to produce clones of a plant in a method known ...

. The hormone NAA does not occur naturally, and, like all auxins, is toxic to plants at high concentrations. In the United States, under the

Federal Insecticide, Fungicide, and Rodenticide Act The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) is a United States federal law that set up the basic U.S. system of pesticide regulation to protect applicators, consumers, and the environment. It is administered and regulated by t ...

(FIFRA), products containing NAA require registration with the

Environmental Protection Agency A biophysical environment is a biotic and abiotic surrounding of an organism or population, and consequently includes the factors that have an influence in their survival, development, and evolution. A biophysical environment can vary in scale f ...

(EPA) as

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...

Use and analysis

NAA is widely used in agriculture for various purposes. It is considered to be only slightly toxic but when at higher concentrations it can be toxic to animals. This was shown when tested on rats via oral ingestion at 1000–5900 mg/kg. NAA has been shown to greatly increase cellulose fiber formation in plants when paired with another phytohormone called gibberellic acid. Because it is in the auxin family it has also been understood to prevent premature dropping and thinning of fruits from stems. It is applied after blossom fertilization. Increased amounts can actually have negative effects however, and cause growth inhibition to the development of plant crops. It has been used on many different crops including apples, olives, oranges, potatoes, and various other hanging fruits. In order for it to obtain its desired effects it must be applied in concentrations ranging from 20–100 μg/mL. NAA present in the environment undergoes oxidation reactions with hydroxyl radicals and sulfate radicals. Radical reactions of NAA were studied using pulse radiolysis technique. Hydroxyl adduct radical was formed as the intermediate during the reaction of hydroxyl radical with NAA. The intermediate naphthyl methyl radical was formed during the reaction of sulfate radical anion with NAA. In

micropropagation Micropropagation or tissue culture is the practice of rapidly multiplying plant stock material to produce many progeny plants, using modern plant tissue culture methods. Micropropagation is used to multiply a wide variety of plants, such as th ...

of various plants, NAA is typically added to a medium containing nutrients essential to the plants' survival. It is added to help induce root formation in various plant types. It can also be applied by spraying it onto plants and which is typical in agricultural use. It is prohibited in many areas to use it in high concentrations due to the health concerns towards humans and other animals. NAA can be detected by

HPLC High-performance liquid chromatography (HPLC), formerly referred to as high-pressure liquid chromatography, is a technique in analytical chemistry used to separate, identify, and quantify each component in a mixture. It relies on pumps to pa ...

-tandem mass spectrometry (HPLC-MS/MS).M.J. Benotti, F.P. Lee, R.A. Rieger, C.R. Iden, C.E. Heine, B.J. Brownawell HPLC/TOF-MS: an alternative to LC/MS/MS for sensitive and selective determination of polar organic contaminants in the aquatic environment Ferrer Imma, E.M. Thurman (Eds.), Liquid Chromatography/Mass Spectrometry, MS/MS and Time of Flight MS, American Chemical Society, New York (2003), pp. 109–127

Derivative uses

*RSD 1000 69191-56-4

References

{{DEFAULTSORT:Naphthaleneacetic acid, 1- Acetic acids Auxins 1-Naphthyl compounds

Use and regulation

Use and analysis

Derivative uses

See also

References