Patent GB-478604-A (GB)
Title: Insecticides
IPC: A01N47/48
Filed: 1936-08-20
Abstract: Polythiocyano derivatives of neutral esters are produced by reacting with an inorganic thiocyanate upon a polyhalogen derivative of the ester in which the halogen atoms are attached to carbon atoms of different radicles, not more than one halogen atom being attached to any one radicle.  The reaction may be effected in a solvent such as absolute alcohol, acetone or methyl isobutyl ketone in which excess of the inorganic thiocyanate, such as sodium thiocyanate, may be suspended.  The initial material may be an ester of a di- or poly-carboxylic acid in which the alcohol radicles or both alcohol and acid radicles contain halogen, esters of di- or poly-hydric alcohols in which the acid radicles contain halogen, or esters of halogen-carboxylic acids with alcohols that may contain halogen.  The radicle carrying the halogen which is to be exchanged for thiocyanogen may be aliphatic, aromatic, or hydroaromatic.  Esters that may be produced include bis-(b -thiocyanoethyl) and bis-(b -thiocyanoethoxyethyl) sebacates and succinates, b -thiocyanoethyl and glyceryl thiocyanacetates, diethylene glycol and ethylene dithiocyanoacetates, and bis-(b -thiocyanoethyl) and bis-(b -thiocyanoethoxyethyl) phthalates.  In examples: (1) bis - (b  - chlorethoxyethyl) sebacate is reacted with sodium thiocyanate in methyl isobutyl ketone; (2) bis-(b -chlorethoxyethyl) succinate is reacted with sodium thiocyanate in a similar manner.  The products are useful for destroying insects and plant fungi. They may be used dissolved in a hydrocarbon such as kerosene or benzene, monobutyl or monoethyl ethylene or diethylene glycol ether or ethylene dichloride and used as a spray or adsorbed in a dry powder for dusting; or as an emulsion with soap, sulphonated oils, or metal alkyl sulphates such as sodium lauryl sulphate; the compound may be dissolved in monoethyl ether of glycol and diluted with a hydrocarbon.  The compounds may be used alone or with pyrethrum, derris, cube, rotenone or other natural insect poison.  The Specification as open to inspection under Sect. 91 includes the production of esters and other organic compounds such as ethers, acetals, ketones, alcohols, amines, sulphides, sulphoxides sulphones &c. containing more than one thiocyano group and mentions a large number of substances of which the following are typical:--acetals such as a -a -bis(b -thiocyanoethoxy) ethane, a  - a  - bis(b -thiocyanoethoxy) - g  - thiocyanopropane, a  - a  - bis(b - thiocyanoethoxy) phenyl methane; ethers such as bis(b -thiocyano)ethyl ether and a  - b  - bis(b  - thiocyanoethoxy-methoxy)ethane; bis(thiocyanoethyl) sulphoxide and sulphide, 2-3-bis(thiocyanoethoxy)dioxane, a  - g  - di(thiocyano)propanol-2 and tris(b -thiocyanoethyl)amine.  There are 17 additional examples describing the preparation of bodies of these types by methods similar to those described in the Specification as accepted.  This subject-matter does not appear in the Specification as accepted.ALSO:Polythiocyano derivatives of neutral esters in which the thiocyano groups are attached to carbon atoms in different radicles, not more than one thiocyano group being attached to any one radicle are used for destroying insects and plant fungi.  They may be used dissolved in a hydrocarbon such as kerosene or benzene, monobutyl or monoethyl ether of ethylene or diethylene glycol, or ethylene chloride, and used as a spray or adsorbed in a dry powder for dusting; or as an emulsion with soap, sulphonated oils, or metal alkyl sulphates such as sodium lauryl sulphate. The thiocyano compound may be dissolved in monoethyl ether of glycol and diluted with a hydrocarbon.  The compounds may be used alone or with pyrethrum, derris, cube, rotenone or other plant insect poison.  The Specification as open to inspection under Sect. 91 includes the use of esters and other organic compounds such as ethers, acetals, ketones, alcohols, amines, sulphides, sulphoxides, sulphones &c. containing more than one thiocyano group, and mentions a large number of which the following are typical: acetals such as a -a -bis(b -thiocyanoethoxy)ethane, a -a -bis(b -thiocyanoethoxy) g -thiocyano propane, and a -a  - bis(b -thiocyanoethoxy)phenyl methane; ethers such as bis(b -thiocyano)ethyl ether and a -b -bis(b -thiocyanoethoxy methoxy) ethane; bis (thiocyanoethyl) sulphoxide and sulphide, 2-3 bis(thiocyanoethoxy) dioxane, a -g -di(thiocyano)propanol-2, p  and bis b -thiocyanoethyl amine.  There are 17 additional examples describing the preparation of bodies of these types. This subject-matter does not appear in the Specification as accepted.