Patent GB-923625-A (GB)
Title: Improvements in or relating to polyacetylenic hydrocarbons
IPC: C07C17/42
Filed: 1959-10-23
Abstract: The Specification comprises polyacetylenic hydrocarbons of the formula <FORM:0923625/III/1> where R1 and R2 are alkylene radicals of 2-50 carbon atoms, n is an integer and the Z's are terminal acetylene groups or together are a single acetylenic radical forming a ring with the remainder of the molecule.  These compounds are formed by reacting a metal acetylide which may be formed in situ with an alkylene dichloride.  In the examples (1) sodium acetylide is reacted with pentamethylene bromide to give 1, 8,-cyclo-tetradecadiyne together with (2) 1, 8, 15-hexa-decatriyne (3) tetramethylene dibromide and sodium acetylide give 1, 7, 13-tetradecatriyne and 1, 7, 13, 19-eicosatetrayne.  The reaction may be effected using 1-3 mols. of dihalide per mol. of acetylide in liquid ammonia, butylamine, ethylenediamine, triethylamine, tetrahydrofuran, ethylene glycol dimethyl ether, dimethyl ether or dioxane.  Ferric nitrate, iron oxide or sodium peroxide may be added as catalyst and temperatures of -50 to 100 DEG C. are used depending on the solvent. Water is added after 3-36 hours and the products extracted.ALSO:Halogenated aromatic hydrocarbons are stabilized against degradation by the addition of 0.0001-5% of a polyacetylenic compound of the formula <FORM:0923625/IV(a)/1> where R1 and R2 are alkylene radicals of 2-50 carbon atoms, or is an integer and the Z's are terminal acetylenic radicals or together are a single acetylenic radical forming a ring with the remainder of the molecule.  In the examples (16) alpha-chloro-p-xylene is stabilized with 1,8,15-hexadecatriyne, (17) alpha - chloro - p-xylene is stabilized with 1,8,15-hexadecatriyne and ethylene glycol, (18) alpha-chloro-p-xylene is stabilized with 1,8,15-hexadecatriyne and bis(2-propynyl) - 2,3,5,6 - tetrachloroterephthalate, (19) benzyl chloride is stabilized with 1,8-cyclo-tetradecadiyne.ALSO:Polyacetylenic hydrocarbons of the formula <FORM:0923625/VI/1> wherein R1 and R2 are alkylene radicals of 2-50 carbon atoms, n is an integer and the Z's are terminal acetylene radicals or together form an acetylene radical forming a ring with the remainder of the molecule, are used as pesticides, insecticides, fungicides, bactericide, nematodicides and selective herbicides in admixture with a carrier.  They may be mixed with other biologically active materials e.g. organic phosphate pesticides, chlorinated hydrocarbon insecticides and foliage and soil fungicides and may be used in liquid sprays emulsifiable concentrates or powder formulations mixed with clays, talc, alumina-silica, water, benzene, toluene, chlorinated benzene, acetone, cyclohexanone, chlorinated xylene, carbon tetrachloride, ethylene dichloride, tetrachloroethylene, carbon disulphide or alcohols.  In liquid formations a wetting agent is preferably added.  The examples describe spray formulations of 1, 7, 13, 19-eicosatetrayne 1,8,15-hexadecatriyne, 1,7,13-tetradecatriyne and 1,8-cyclododecadiyne and their uses against insects and other pests, bacteria, fungi, and non-plant parasitic nematodes and as selective herbicides.