N-lower alkyl neodecanamide insect repellents
AssigneeColgate-Palmolive Company
InventorRobert J. Steltenkamp
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AssigneeColgate-Palmolive Company
InventorRobert J. Steltenkamp
Estimating the term…
N-lower alkyl neoalkanamides (N-lower alkyl trialkylacetamides of certain types) of 1 to 4 carbon atoms in the lower alkyl thereof and of 5 to 14 carbon atoms in the neoalkanoyl (or trialkylacetyl) group, e.g., N-methyl- and N-ethyl neodecanamides and N-methyl and N-ethyl neotridecanamides, are new compounds, secondary amides which have insect repellent properties, being especially effective against cockroaches, e.g., the German cockroach. However, they are also useful as repellents for other insects, including American cockroaches, mosquitoes, flies, fleas, ants, and lice. Additionally, they may repel arachnids, such as spiders, ticks and mites. The new neoalkanamides may be synthesized easily, as by reacting a primary lower alkyl amine with a neoalkanoyl halide, e.g. by reacting methyl amine or ethyl amine with neodecanoyl chloride. The most effective of the described amides for insect repellency are normally liquid and are sufficiently volatile to be detectable in air by insects. They may be applied directly to surfaces to be treated or they may be incorporated in detergent compositions, such as built laundry detergents, floor and wall cleaners, rug cleaners and shampoos, hair shampoos, and liquid and bar soaps, and have been found to be sufficiently substantive to the substrate being washed so as to impart insect repelling properties to it.
Insect repellent compounds which are liquid at room temperature and of the formula ##STR3## wherein R, R' and R" are alkyls and the sum of the carbon atoms therein is eight, and wherein R"' is methyl, ethyl or a mixture thereof, and wherein the acyl moiety, ##STR4## of such formula, is a mixture of acyls of corresponding acids of the formula ##STR5## wherein in about 31% of the neodecanoic acid R is hexyl and R' and R" are both methyl, in about 67% of the neodecanoic acid R' is methyl, R" is alkyl of a carbon atoms content greater than that of methyl and less than that of R, and R is of a carbon atoms content less than that of hexyl, and in about 2% of the neodecanoic acid R' and R" are both of a carbon atoms content greater than that of methyl and less than that of R, and R is of a carbon atoms content less than that of hexyl.
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