Patent GB-785332-A (GB)
Title: Improvements in or relating to defoliants
IPC: C07C29/42
Filed: 1955-05-20
Abstract: Compounds having the formula <FORM:0785332/IV (a)/1> in which R and R1 can be the same or different and can be hydrogen or aliphatic, alicyclic, aromatic or heterocyclic groups, preferably unsubstituted alkyl, alkenyl, aryl, cycloalkyl or substituted by halogen, hydroxy, substituted hydroxy, carboxy, substituted carboxy, nitro or amino groups; X and Y can be the same or different and can be hydrogen, any of the organic groups described for R and R1, preferably hydrocarbonaceous, and can also be salt-forming groups either inorganic or organic, e.g. metallic, preferably alkali metal, ions, ammonium or substituted ammonium ions, are prepared by reaction of acetylene with aldehydes.  In examples, 1,4-butynediol is prepared by reacting acetylene with two mols. of formaldehyde and may be converted to its salts, e.g. its disodium and bis-tetraethylammonium salts, 1,4-dimethyl - 1,4 - butynediol is prepared by reaction of two mols. acetaldehyde with acetylene, and 1-methyl-4-phenyl-1,4-butynediol by reaction of 1 mol. acetaldehyde and 1 mol. benzaldehyde with acetylene.  Compounds having one or both of the hydroxyl hydrogens replaced by an organic group are prepared by reacting the corresponding diol with sodium alcoholate to form the sodium salt of the diol which can then be reacted with an organic halide to yield the ether derivative.  In examples, 1 mol. of 1-butyl-1 : 4-butynediol is reacted with 2 mols. of sodium ethoxide and the product with 2 mols. of ethyl bromide to produce 1,4 - diethoxy - 1 - butylbutyne - 2 ; 1 mol. of 1,4 - butynediol is reacted with 1 mol. of sodium methylate and the monosodium salt thus formed is reacted with 1 mol. of n-butyl bromide to yield 1 - butoxy - 4 - hydroxy - butyne - 2.  Additional compounds are listed (see Group VI).ALSO:A defoliation composition comprises a conditioning agent and, as an active defoliation ingredient, a compound having the grouping -O-CH-C=C-CH-O-, e.g. a compound of the formula <FORM:0785332/VI/1> in which R and R1 can be the same or different and can be hydrogen or aliphatic, alicyclic, aromatic or heterocyclic groups, preferably unsubstituted alkyl, alkenyl, aryl, cycloalkyl or substituted, e.g. by halogen, hydroxy, substituted hydroxy, carboxy, substituted carboxy, nitro, or amino groups, X and Y can be the same or different and can be hydrogen, any of the organic groups described for R and R1, preferably hydrocarbonaceous, and can also be salt-forming groups either inorganic or organic, e.g. metallic, preferably alkali metal, ions, ammonium or substituted ammonium ions. The conditioning agent provides a dispersing or surface-contacting action without phytotaxic effect and includes inert organic and inorganic dusts or powders, hydrocarbon liquids or oils and organic solvents. Specified active ingredients are 1,4-butynediol, 1,4-dimethyl-1, 4-butynediol, 1-ethyl - 1,4 - butynediol, 1 - butyl - 1,4 - butynediol, 1 - hexyl - 1,4 - butynediol, 1 - dodecyl - 1,4 - butynediol, 1 - phenyl - 1,4 - butynediol, 1 - p - tolyl - 1,4 - butynediol, 1 - methyl - 4 - ethyl - 1,4 - butynediol, 1 - methyl - 4 - amyl - 1,4 - butynediol, 1 - methyl - 4 - dodecyl - 1,4 - butynediol, 1 - butyl - 4 - octyl - 1,4 - butynediol, 1,4 - diisopropyl - 1,4 - butynediol, 1,4 - dimethoxy - butyne - 2, 1,4 - diphenoxy - butyne-2, 1 - methoxy - 4 - p - chlorophenoxy - butyne-2, 1 - butoxy - 4 - phenoxy - 1 - methyl - butyne-2, 1,4-diphenyl-1,4-diphenoxy-butyne-2, 1-methoxy - 4 - hydroxy - butyne - 2, 1 - hexoxy-4 - hydroxy - 4 - amyl - butyne - 2, disodium-1,4-butynediol, calcium-1,4-butynediol, potassium-1,4-butynediol, amyl-1,4-butynediol, pyridinium - 1,4 - butynediol, trimethyl - amyl - 1 - phenyl - 1,4 - butynediol, 1 - (g - pyridyl) - 1,4 - butynediol.