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Ethyl butylacetylaminopropionate is an
insect repellent An insect repellent (also commonly called "bug spray" or "bug deterrent") is a substance applied to the skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellent ...
whose trade name is IR3535 and was developed and commercialized by
Merck KGaA The Merck Group, branded and commonly known as Merck, is a German Multinational corporation, multinational science and technology company headquartered in Darmstadt, with about 60,000 employees and a presence in 66 countries. The group include ...
(Germany). It is a colorless and odorless oil with a good skin feel in final products, and it is
biodegradable Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. It is generally assumed to be a natural process, which differentiates it from composting. Composting is a human-driven process in which biodegrada ...
.Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
/ref>3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
/ref>3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet
/ref> Unlike
icaridin Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A s ...
, IR3535 can dissolve some plastics and synthetic fabrics, except
polyethylene Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including bott ...
and
polypropylene Polypropylene (PP), also known as polypropene, is a thermoplastic polymer used in a wide variety of applications. It is produced via chain-growth polymerization from the monomer Propene, propylene. Polypropylene belongs to the group of polyolefin ...
.


Effectiveness

IR3535 is effective in repelling several different insects such as mosquitoes species and also
midges A midge is any small fly, including species in several families of non-mosquito nematoceran Diptera. Midges are found (seasonally or otherwise) on practically every land area outside permanently arid deserts and the frigid zones. Some midg ...
,
ticks Ticks are parasitic arachnids of the order Ixodida. They are part of the mite superorder Parasitiformes. Adult ticks are approximately 3 to 5 mm in length depending on age, sex, and species, but can become larger when engorged. Ticks a ...
and
head lice The head louse (''Pediculus humanus capitis'') is an obligate ectoparasite of humans. Head lice are wingless insects that spend their entire lives on the human scalp and feed exclusively on human blood. Humans are the only known hosts of this s ...
. It is as effective as
DEET ''N'',''N''-Diethyl-''meta''-toluamide, also called diethyltoluamide or DEET (, from DET, the initials of di- + ethyl + toluamide), is the oldest, one of the most effective, and most common active ingredients in commercial insect repellents. ...
against ''
Aedes ''Aedes'' (also known as the tiger mosquito) is a genus of mosquitoes originally found in tropical and subtropical zones, but now found on all continents except Antarctica. Some species have been spread by human activity: ''Aedes albopictus'', ...
'' and ''
Culex ''Culex'' or typical mosquitoes are a genus of mosquitoes, several species of which serve as vectors of one or more important diseases of birds, humans, and other animals. The diseases they vector include arbovirus infections such as West Nil ...
'' mosquitoes, but may be less effective than DEET against ''
Anopheles ''Anopheles'' () is a genus of mosquito first described by the German entomologist Johann Wilhelm Meigen, J. W. Meigen in 1818, and are known as nail mosquitoes and marsh mosquitoes. Many such mosquitoes are Disease vector, vectors of the paras ...
'' mosquitoes, vectors of
malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...
. A 2013 review concluded that IR3535 is as effective as 20%
DEET ''N'',''N''-Diethyl-''meta''-toluamide, also called diethyltoluamide or DEET (, from DET, the initials of di- + ethyl + toluamide), is the oldest, one of the most effective, and most common active ingredients in commercial insect repellents. ...
against ''Anopheles'', citing that some studies reported possibly shorter protection of just 3.8 hours. In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20%
icaridin Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A s ...
instead of IR3535. IR3535, among other repellents, is included in the
World Health Organization The World Health Organization (WHO) is a list of specialized agencies of the United Nations, specialized agency of the United Nations which coordinates responses to international public health issues and emergencies. It is headquartered in Gen ...
(WHO) recommendation for areas with malaria. The WHO also notes that it may be necessary to reapply repellents every 3-4 hours in hot and humid climates. IR3535 also helps prevent bites from ticks that may transmit
Lyme disease Lyme disease, also known as Lyme borreliosis, is a tick-borne disease caused by species of ''Borrelia'' bacteria, Disease vector, transmitted by blood-feeding ticks in the genus ''Ixodes''. It is the most common disease spread by ticks in th ...
.


Adverse effects

IR3535 can irritate the eyes on contact.


Interactions

Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.


Mechanism of action

The mechanism of action is still under investigation, but it probably related to the intolerance of mosquitos and other invertebrate animals to its odor. IR3535 is applied topically in human skin and prevent bites from mosquitos and ticks that might cause serious diseases, such as
dengue Dengue fever is a mosquito-borne disease caused by dengue virus, prevalent in tropical and subtropical areas. Asymptomatic infections are uncommon, mild cases happen frequently; if symptoms appear, they typically begin 3 to 14 days after ...
,
malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...
,
zika Zika fever, also known as Zika virus disease or simply Zika, is an infectious disease caused by the Zika virus. Most cases have no symptoms, but when present they are usually mild and can resemble dengue fever. Symptoms may include fever, conju ...
,
West Nile virus West Nile virus (WNV) is a single-stranded RNA virus that causes West Nile fever. It is a member of the family ''Flaviviridae'', from the genus ''Flavivirus'', which also contains the Zika virus, dengue virus, and yellow fever virus. The virus ...
,
Lyme disease Lyme disease, also known as Lyme borreliosis, is a tick-borne disease caused by species of ''Borrelia'' bacteria, Disease vector, transmitted by blood-feeding ticks in the genus ''Ixodes''. It is the most common disease spread by ticks in th ...
, among others.


Chemistry

IR3535 is a
derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...
of the non-proteinogenic amino acid beta-alanine.


Approval

IR3535 is approved by several authorities around the world, including
ECHA The European Chemicals Agency (ECHA; ) is an agency of the European Union working for the safe use of chemicals. It manages the technical and administrative aspects of the implementation of the European Union regulation called Registration, ...
(Europe) and the EPA (US) where it is considered a biopesticide.


See also

*
DEET ''N'',''N''-Diethyl-''meta''-toluamide, also called diethyltoluamide or DEET (, from DET, the initials of di- + ethyl + toluamide), is the oldest, one of the most effective, and most common active ingredients in commercial insect repellents. ...
*
Icaridin Icaridin, also known as picaridin, is an insect repellent which can be used directly on skin or clothing. It has broad efficacy against various arthropods such as mosquitos, ticks, gnats, flies and fleas, and is almost colorless and odorless. A s ...
*
p-Menthane-3,8-diol ''p''-Menthane-3,8-diol, also known as ''para''-menthane-3,8-diol, PMD, or menthoglycol, is an organic compound classified as a diol and a terpenoid. It is colorless. Its name reflects the hydrocarbon backbone, which is that of ''p''-menthane ...
(PMD) *
Permethrin Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects ...
, a
pyrethroid A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums (''Chrysanthemum cinerariaefolium'' and ''Chrysanthemum coccineum, C. coccineum''). Pyrethroids are used as commercial and hou ...
insecticide Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, i ...
that can be applied to clothing to help prevent bites :


References


External links

* {{cite journal , doi = 10.1603/0022-2585-39.6.895 , pmid = 12495189 , url = http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf , archive-url = https://web.archive.org/web/20110721072133/http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf , url-status = dead , archive-date = 2011-07-21 , title = Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and DEET to Black Salt Marsh Mosquitoes (Diptera: Culicidae) in the Everglades National Park, journal = Journal of Medical Entomology, volume = 39, issue = 6, pages = 895–899, year = 2002, last1 = Barnard, first1 = Donald R., last2 = Bernier, first2 = Ulrich R., last3 = Posey, first3 = Kenneth H., last4 = Xue, first4 = Rui-De, doi-access = free
Tick Bite Prevention & the Use of Insect Repellents
Biopesticides Insect repellents Acetamides Ethyl esters