''N'',''N''-Diethyl-''meta''-toluamide, also called DEET () or diethyltoluamide, is the most common active ingredient in

insect repellent An insect repellent (also commonly called "bug spray") is a substance applied to skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellents help prevent and cont ...

s. It is a slightly yellow oil intended to be applied to the

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other cuticle, animal coverings, such as the arthropod exoskeleton, have diffe ...

or to

clothing Clothing (also known as clothes, apparel, and attire) are items worn on the body. Typically, clothing is made of fabrics or textiles, but over time it has included garments made from animal skin and other thin sheets of materials and natural ...

and provides protection against

mosquito Mosquitoes (or mosquitos) are members of a group of almost 3,600 species of small flies within the family Culicidae (from the Latin ''culex'' meaning " gnat"). The word "mosquito" (formed by ''mosca'' and diminutive ''-ito'') is Spanish for "li ...

es, flies,

tick Ticks (order Ixodida) are parasitic arachnids that are part of the mite superorder Parasitiformes. Adult ticks are approximately 3 to 5 mm in length depending on age, sex, species, and "fullness". Ticks are external parasites, living by ...

flea Flea, the common name for the order Siphonaptera, includes 2,500 species of small flightless insects that live as external parasites of mammals and birds. Fleas live by ingesting the blood of their hosts. Adult fleas grow to about long, a ...

chiggers ''Trombicula'', known as chiggers, red bugs, scrub-itch mites, or berry bugs, are small arachnids (eight-legged arthropods) in the Trombiculidae family. In their larval stage, they attach to various animals, including humans, and feed on skin, ...

leeches Leeches are segmented parasitic or predatory worms that comprise the subclass Hirudinea within the phylum Annelida. They are closely related to the oligochaetes, which include the earthworm, and like them have soft, muscular segmented bo ...

and many biting insects.

History

DEET was developed in 1944 by Samuel Gertler of the

United States Department of Agriculture The United States Department of Agriculture (USDA) is the United States federal executive departments, federal executive department responsible for developing and executing federal laws related to farming, forestry, rural economic development, ...

for use by the

United States Army The United States Army (USA) is the land service branch of the United States Armed Forces. It is one of the eight U.S. uniformed services, and is designated as the Army of the United States in the U.S. Constitution.Article II, section 2, cla ...

, following its experience of

jungle warfare Jungle warfare is a term used to cover the special techniques needed for military units to survive and fight in jungle terrain. It has been the topic of extensive study by military strategists, and was an important part of the planning for bo ...

during

World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposin ...

. It was originally tested as a pesticide on farm fields, and entered military use in 1946 and civilian use in 1957. It was used in

Vietnam Vietnam or Viet Nam ( vi, Việt Nam, ), officially the Socialist Republic of Vietnam,., group="n" is a country in Southeast Asia, at the eastern edge of mainland Southeast Asia, with an area of and population of 96 million, making i ...

and Southeast Asia. In its original form, known as "bug juice", the application solution was composed of 75% DEET and 25% ethanol. Later, a new version of the repellent was developed by the U.S. Army and the USDA. This formulation consisted of DEET and a mixture of polymers that extended its release and reduced its evaporation rate. This extended-release application was registered by 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 ...

in 1991.

Preparation

A slightly yellow liquid at

room temperature Colloquially, "room temperature" is a range of air temperatures that most people prefer for indoor settings. It feels comfortable to a person when they are wearing typical indoor clothing. Human comfort can extend beyond this range depending on ...

, it can be prepared by converting ''m''-toluic acid (3-methylbenzoic acid) to the corresponding

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

using

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

(SOCl₂), and then allowing that product to react with

diethylamine Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to im ...

: :

Mechanism and effectiveness

DEET is an extremely effective insect repellant, the most effective available. It is effective against a variety of invertebrates, including ticks, flies, mosquitos, and some parasitic worms. DEET is suspected to affect two pathways in mosquitos: it affects

odorant receptors Olfactory receptors (ORs), also known as odorant receptors, are chemoreceptors expressed in the cell membranes of olfactory receptor neurons and are responsible for the detection of odorants (for example, compounds that have an odor) which give ri ...

at a distance, and it affects

chemoreceptors A chemoreceptor, also known as chemosensor, is a specialized sensory receptor which transduces a chemical substance (endogenous or induced) to generate a biological signal. This signal may be in the form of an action potential, if the chemorecept ...

upon contact. The exact mechanisms are still being researched, but the two most likely hypotheses are the "smell and avoid hypothesis" (that DEET has an unpleasant odor to insects), and the "confusant hypothesis" (that smelling DEET confuses insects).

Concentrations

The concentration of DEET in products may range from less than 10 percent to nearly 100 percent. Concentrations of 10 to 30 percent are recommended for infants and children. DEET should not be used on children under 2 months of age. DEET is often sold and used in spray or lotion in concentrations up to 100%. ''

Consumer Reports Consumer Reports (CR), formerly Consumers Union (CU), is an American nonprofit consumer organization dedicated to independent product testing, investigative journalism, consumer-oriented research, public education, and consumer advocacy. Founded ...

'' found a direct

correlation In statistics, correlation or dependence is any statistical relationship, whether causal or not, between two random variables or bivariate data. Although in the broadest sense, "correlation" may indicate any type of association, in statistics ...

between DEET concentration and hours of protection against insect bites. 100% DEET was found to offer up to 12 hours of protection while several lower concentration DEET formulations (20–34%) offered 3–6 hours of protection. Other research has corroborated the effectiveness of DEET. The Centers for Disease Control and Prevention recommends 30–50% DEET to prevent the spread of pathogens carried by insects. A 2008 study found that higher concentrations of DEET have an improved ability to repel insects through fabric.

Effects on health

As a precaution, manufacturers advise that DEET products should not be used under clothing or on damaged skin, and that preparations be washed off after they are no longer needed or between applications. DEET can act as an irritant; in rare cases, it may cause severe

epidermal The epidermis is the outermost of the three layers that comprise the skin, the inner layers being the dermis and hypodermis. The epidermis layer provides a barrier to infection from environmental pathogens and regulates the amount of water relea ...

reactions. Other symptoms that can occur are breathing difficulty, burning eyes, or

headache Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches. Headaches can occur as a result ...

s. The authors of a 2002 study published in ''

The New England Journal of Medicine ''The New England Journal of Medicine'' (''NEJM'') is a weekly medical journal published by the Massachusetts Medical Society. It is among the most prestigious peer-reviewed medical journals as well as the oldest continuously published one. His ...

'' wrote:

... this repellent has been subjected to more scientific and toxicologic scrutiny than any other repellent substance. ... DEET has a remarkable safety profile after 40 years of use and nearly 8 billion human applications. Fewer than 50 cases of serious toxic effects have been documented in ... medical literature since 1960 ... Many of these cases of toxic effects involved long-term, heavy, frequent, or whole-body application of DEET. No correlation has been found between the concentration of DEET used and the risk of toxic effects. ... When applied with common sense, DEET-based repellents can be expected to provide a safe as well as a long-lasting repellent effect ... under circumstances in which it is crucial to be protected against arthropod bites that might transmit disease.

When DEET is used in combination with insecticides for

cockroach Cockroaches (or roaches) are a paraphyletic group of insects belonging to Blattodea, containing all members of the group except termites. About 30 cockroach species out of 4,600 are associated with human habitats. Some species are well-known as ...

es it can strengthen the toxicity of

carbamate In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...

, an

acetylcholinesterase Acetylcholinesterase (HGNC symbol ACHE; EC 3.1.1.7; systematic name acetylcholine acetylhydrolase), also known as AChE, AChase or acetylhydrolase, is the primary cholinesterase in the body. It is an enzyme Enzymes () are proteins that a ...

inhibitor. These 1996 findings indicate that DEET has

neurological Neurology (from el, νεῦρον (neûron), "string, nerve" and the suffix -logia, "study of") is the branch of medicine dealing with the diagnosis and treatment of all categories of conditions and disease involving the brain, the spinal ...

effects on insects in addition to known

olfactory The sense of smell, or olfaction, is the special sense through which smells (or odors) are perceived. The sense of smell has many functions, including detecting desirable foods, hazards, and pheromones, and plays a role in taste. In humans, it ...

effects, and that its toxicity is strengthened in combination with other insecticides. In the DEET Reregistration Eligibility Decision (RED) in 1998, the

United States Environmental Protection Agency The Environmental Protection Agency (EPA) is an independent executive agency of the United States federal government tasked with environmental protection matters. President Richard Nixon proposed the establishment of EPA on July 9, 1970; it be ...

(EPA) reported 14 to 46 cases of potential DEET-associated

seizure An epileptic seizure, informally known as a seizure, is a period of symptoms due to abnormally excessive or synchronous neuronal activity in the brain. Outward effects vary from uncontrolled shaking movements involving much of the body with los ...

s, including four deaths. The EPA states: "... it does appear that some cases are likely related to DEET

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

," which may underreport the risk as physicians may fail to check for history of DEET use or fail to report cases of seizure subsequent to DEET use. In 1997, the Pesticide Information Project of Cooperative Extension Offices of

Cornell University Cornell University is a private statutory land-grant research university based in Ithaca, New York. It is a member of the Ivy League. Founded in 1865 by Ezra Cornell and Andrew Dickson White, Cornell was founded with the intention to teach an ...

stated that "

Everglades National Park Everglades National Park is an American national park that protects the southern twenty percent of the original Everglades in Florida. The park is the largest tropical wilderness in the United States and the largest wilderness of any kind east ...

employees having extensive DEET exposure were more likely to have

insomnia Insomnia, also known as sleeplessness, is a sleep disorder in which people have trouble sleeping. They may have difficulty falling asleep, or staying asleep as long as desired. Insomnia is typically followed by daytime sleepiness, low energy, ...

, mood disturbances and impaired

cognitive function Cognitive skills, also called cognitive functions, cognitive abilities or cognitive capacities, are brain-based skills which are needed in acquisition of knowledge, manipulation of information and reasoning. They have more to do with the mechanisms ...

than lesser exposed co-workers". When used as directed, products containing between 10% and 30% DEET have been found by the

American Academy of Pediatrics The American Academy of Pediatrics (AAP) is an American professional association of pediatricians, headquartered in Itasca, Illinois. It maintains its Department of Federal Affairs office in Washington, D.C. Background The Academy was founded ...

to be safe to use on children, as well as adults, but the Academy recommends that DEET not be used on infants less than two months old. Citing human health reasons,

Health Canada Health Canada (HC; french: Santé Canada, SC)Health Canada is the applied title under the Federal Identity Program; the legal title is Department of Health (). is the Structure of the Canadian federal government#Departments, with subsidiary unit ...

barred the sale of insect repellents for human use that contained more than 30% DEET in a 2002 re-evaluation "based on a human health risk assessment that considered daily application of DEET over a prolonged period of time". The agency recommended that DEET-based products be used on children between the ages of 2 and 12 only if the

concentration In chemistry, concentration is the abundance of a constituent divided by the total volume of a mixture. Several types of mathematical description can be distinguished: '' mass concentration'', ''molar concentration'', ''number concentration'', an ...

of DEET is 10% or less and that repellents be applied no more than 3 times a day, children under 2 should not receive more than 1 application of repellent in a day and DEET-based products of any concentration should not be used on infants under 6 months. Some experts recommend against applying DEET and sunscreen simultaneously since that would increase DEET penetration; Xiaochen Gu, a professor at the

University of Manitoba The University of Manitoba (U of M, UManitoba, or UM) is a Canadian public research university in the province of Manitoba.University of Florida The University of Florida (Florida or UF) is a public land-grant research university in Gainesville, Florida. It is a senior member of the State University System of Florida, traces its origins to 1853, and has operated continuously on its ...

's College of Public Health and Health Professions analyzed data from the National Health and Nutrition Examination Survey and identified 1,205 participants who had "DEET metabolic levels recorded at or above detection limits". They analyzed

biomarker In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, ...

s related to systemic inflammation, immune, liver, and kidney functions, and found no "evidence that DEET exposure has any impact on the biomarkers identified."

Detection in body fluids

DEET may be measured in blood, plasma, or urine by gas or liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma DEET concentrations are expected to be in a range of 0.3–3.0 mg/L during the first 8 hours after dermal application in persons using the chemical appropriately, >6 mg/L in intoxicated patients and >100 mg/L in victims of acute intentional oral overdose.

Effects on materials

DEET is an effective

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

, and may dissolve some watch crystals, plastics,

rayon Rayon is a semi-synthetic fiber, made from natural sources of regenerated cellulose, such as wood and related agricultural products. It has the same molecular structure as cellulose. It is also called viscose. Many types and grades of viscose f ...

spandex Spandex, Lycra, or elastane is a synthetic fiber known for its exceptional elasticity. It is a polyether-polyurea copolymer that was invented in 1958 by chemist Joseph Shivers at DuPont's Benger Laboratory in Waynesboro, Virginia, US. The ge ...

, other synthetic fabrics, and painted or

varnish Varnish is a clear transparent hard protective coating or film. It is not a stain. It usually has a yellowish shade from the manufacturing process and materials used, but it may also be pigmented as desired, and is sold commercially in various ...

ed surfaces including nail polish. It also may act as a

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

by remaining inside some formerly hard plastics, leaving them softened and more flexible. DEET is incompatible with rayon,

acetate An acetate is a salt (chemistry), salt formed by the combination of acetic acid with a base (e.g. Alkali metal, alkaline, Alkaline earth metal, earthy, Transition metal, metallic, nonmetallic or radical Radical (chemistry), base). "Acetate" als ...

, or

dynel Dynel is a trade name for a type of synthetic fiber used in fibre reinforced plastic composite materials, especially for marine applications. As it is easily dyed, it was also used to fabricate wigs. The fashion designer Pierre Cardin used Dynel f ...

clothing.

Effects on the environment

Though DEET is not expected to

bioaccumulate Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance at a rate faster than that at which the substance is lost or eliminated ...

, it has been found to have a slight

for fresh-water

fish Fish are aquatic, craniate, gill-bearing animals that lack limbs with digits. Included in this definition are the living hagfish, lampreys, and cartilaginous and bony fish as well as various extinct related groups. Approximately 95% of li ...

such as

rainbow trout The rainbow trout (''Oncorhynchus mykiss'') is a species of trout native to cold-water tributaries of the Pacific Ocean in Asia and North America. The steelhead (sometimes called "steelhead trout") is an anadromous (sea-run) form of the coasta ...

and

tilapia Tilapia ( ) is the common name for nearly a hundred species of cichlid fish from the coelotilapine, coptodonine, heterotilapine, oreochromine, pelmatolapiine, and tilapiine tribes (formerly all were "Tilapiini"), with the economically most ...

, and it also has been shown to be toxic for some species of freshwater

zooplankton Zooplankton are the animal component of the planktonic community ("zoo" comes from the Greek word for ''animal''). Plankton are aquatic organisms that are unable to swim effectively against currents, and consequently drift or are carried along by ...

. DEET has been detected at low concentrations in water bodies as a result of production and use, such as in the

Mississippi River The Mississippi River is the second-longest river and chief river of the second-largest drainage system in North America, second only to the Hudson Bay drainage system. From its traditional source of Lake Itasca in northern Minnesota, it f ...

and its tributaries, where a 1991 study detected levels varying from 5 to 201 ng/L. A 1975 study analyzed the effects of DEET on communities of freshwater organisms native to Chinese waterways and found that compared to other commercial insect repellants, DEET was moderately toxic to aquatic organisms. The most-at-risk organisms were

algae Algae (; singular alga ) is an informal term for a large and diverse group of photosynthetic eukaryotic organisms. It is a polyphyletic grouping that includes species from multiple distinct clades. Included organisms range from unicellular mic ...

colonies which often experienced "significant biomass decline and community composition shift when exposed to DEET at 500 ng/L.

References

External links

DEET General Fact Sheet - National Pesticide Information Center

DEET Technical Fact Sheet – National Pesticide Information Center

West Nile Virus Resource Guide – National Pesticide Information Center

US Environmental Protection Agency information on DEET

(from a

RAND Corporation The RAND Corporation (from the phrase "research and development") is an American nonprofit global policy think tank created in 1948 by Douglas Aircraft Company to offer research and analysis to the United States Armed Forces. It is financed ...

report on

Gulf War The Gulf War was a 1990–1991 armed campaign waged by a 35-country military coalition in response to the Iraqi invasion of Kuwait. Spearheaded by the United States, the coalition's efforts against Iraq were carried out in two key phases: ...

illnesses)
Health Canada - Re-evaluation Decision Document: Personal insect repellents containing DEET (N,N-diethyl-m-toluamide and related compounds), 2002
{{DEFAULTSORT:Deet Household chemicals Insect repellents Benzamides 3-Tolyl compounds