Description
Ethyl butylacetylaminopropionate (IR3535) is effective against several insects and is considered an alternative repellent to DEET and Icaridin, thanks to its very low toxicity and equal efficacy. Officially considered safe and effective for use in children over 2 months of age and pregnant and breastfeeding women by the World Health Organization, this repellent has been used in Europe for over 30 years, and its use has been increasing worldwide[1].
Physical properties
Ethyl butylacetylaminopropionate is a natural product found in Averrhoa bilimbi with data available.
History
Ethyl butylacetylaminopropionate is a synthetic molecule derived from a natural amino acid, b-alanine, and its alternative chemical formula name is beta-alanine, n-acetyl-N-butyl-ethyl ester. It is known as IR3535 or EBAAP in the literature. This molecule was developed in the early 1970s using targeted molecular design following functional structure guidelines similar to those reported by Boeckh.1 In his study, repellency of a chemical was correlated with a structural pattern consisting of an amide group linked by a lipophilic chain to an sp3 (i.e., an oxygen atom without a double bond) hybridized oxygen within a group such as hydroxyl or ester. IR3535 repellent (hereafter referred to as IR3535) is currently used in over 150 consumer products world-wide. Despite its commercial history of more than 10 years world-wide and 25 years in European countries, IR3535 has been introduced as a product in the U.S. only recently (1999).
Uses
Ethyl Butylacetylaminopropionate is an insect repellent for application to human skin and clothing in public health applications, to repel biting arthropods such as mosquitoes, flies and ticks.
Definition
ChEBI: Ethyl 3-(N-butylacetamido)propionate is a tertiary carboxamide, a member of acetamides and an ethyl ester.
Production Methods
Quwenzhi is commercially produced through esterification of N-acetyl-N-butyl-beta-alanine with ethanol. The process begins with the synthesis of N-acetyl-N-butyl-beta-alanine, which is then reacted with ethanol in the presence of acid catalysts to form the ethyl ester. This reaction is typically conducted under controlled temperature and pressure to optimise yield and purity.
Mechanism of action
Repellent activity but exact mode of action is unclear
Safety
Ethyl butylacetylaminopropionate (IR3535) is a transparent, colourless, odourless liquid mixture proven safe, as demonstrated by acute toxicity, local tolerability, phototoxicity and repeated-dose toxicity assays. Further, IR3535 is non-genotoxic and has thus been considered a safe insect-repellent ingredient by the US Environmental Protection Agency since 1999. Moreover, this compound is classified as a hypoallergenic substance based on skin irritation tests. IR3535 is mainly used as a mosquito/mite repellent sprayed on the body or clothing during outdoor activities. This compound does not have a sticky texture or an offensive odour, which makes it uniquely well-suited for topical use. Further, the effects of IR3535-based insect repellents can last up to 4 h with a single spray. IR3535 is yet to be linked to any toxic effects and is thus considered safe even in cases of exposure via ingestion, inhalation or skin penetration[2].
References
[1] Renata Colombo, Alanis Tiozzo Souza. “Degradation of ethyl butylacetylaminopropionate (IR3535) during chlorination: Tentative identification and toxicity prediction of its disinfection by-products.” Chemosphere 280 (2021): Article 130656.
[2] Bhanu Shrestha. “Cellular and molecular basis of IR3535 perception in Drosophila.” Pest Management Science 78 2 (2021): 793–802.
Pesticide Type
Insecticide
