Patent GB-480528-A (GB)
Title: Insecticides
IPC: C07C331/02
Filed: 1936-08-20
Abstract: Polythiocyano compounds are produced by reacting an inorganic thiocyanate with an aliphatic polyhalogen compound having a chain of at least four carbon atoms interrupted by at least one ether oxygen atom, a sulphur atom or a nitrogen atom, each group of carbon atoms containing not more than one halogen atom.  The reaction may be effected in a solvent such as alcohol or acetone, and a catalyst such as copper may be used.  Excess of the inorganic thiocyanate may be employed, suspended in the solvent. The initial material may be a di- or poly-halogen derivative of an acetal, ether, sulphoxide, or amine, or of dioxane, many of which are indicated.  Examples describe the production of b -b 1-dithiocyanodiethyl ether, a -b -bis-(b -thiocyano-ethoxy-methoxy)-ethane, bis-(b -thiocyanoethyl)-sulphoxide, 2-3-bis-(b -thiocyanoethoxy)-dioxane, bis-(b -thiocyanoethoxy)-methane, a -a -bis-(b -thiocyanoethoxy) - ethane, a  - a  - bis - (b -thiocyanoethoxy) - b  - methyl propane, a - a  - bis-(b  - thiocyanoethoxy) - butane, a  - a  - bis - (b -thiocyanoethoxy) - heptane, a  - a  - bis - (b -thiocyanoethoxy)-g -thiocyano propane, a -a -bis-(b -thiocyanoethoxy)-butene-2, bis-(g -thiocyanopropoxy)-methane, a -a -bis-(g -thiocyanopropoxy) - b  - methyl propane, tris - (b  - thiocyanoethyl)-amine, and bis - (b  - thiocyanoethyl)-sulphide.  The products are useful for destroying insects and plant fungi.  They may be used dissolved in a hydrocarbon such as kerosene or benzene, the monobutyl and monoethyl ethers of ethylene glycol and diethylene glycol, 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 alkali metal alkyl sulphates such as sodium lauryl sulphate; the thiocyano compound may be dissolved in the monoethyl ether of ethylene glycol and diluted with a hydrocarbon.  The compounds may be used alone or with pyrethrum, derris, cube, rotenone or other natural insect poisons.  2-3-bis-(b -Chlorethoxy)-dioxane may be made from 2-3 dichlordioxane and ethylene chlorhydrin in the presence of calcium carbonate.  a -a -bis-(b  - Chlorethoxy) - butene-2 may be made from a mixture of crotonaldehyde, ethylene chlorhydrin, calcium chloride and formic acid.  The Specification as open to inspection under Sect. 91 is not p  limited to aliphatic compounds of the kind described above, and includes an example for the production of bis-(b -thiocyanoethoxy)-phenyl methane and includes also the production of the esters described in Specification 478,604. This subject-matter does not appear in the Specification as accepted.ALSO:Polythiocyano aliphatic compounds having a chain of at least four carbon atoms interrupted by at least one ether oxygen atom, a sulphur atom or a nitrogen atom, each group of carbon atoms containing not more than one thiocyano group are employed for p  destroying insects and fungi. They may be used dissolved in a hydrocarbon such as kerosene or benzene, the monobutyl and monoethyl ethers of ethylene glycol and diethylene glycol 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 alkali metal alkyl sulphates such as sodium lauryl sulphate; the thiocyano compound may be dissolved in the monoethyl ether of ethylene glycol and diluted with a hydrocarbon. The compounds may be used alone or with pyrethrum, derris, cube, rotenone, or other natural insect poisons.  The compounds specified include the polythiocano derivatives of acetals, ethers, sulphoxides, sulphates and amines, and of dioxane, many of which are mentioned. Examples describe the production of b -b 1-dithiocyano-diethyl ether, a -b -bis (b -thiocyano-ethoxy-methoxy) ethane, bis(b -thiocyanoethyl) sulphide, 2-3-bis (b -thiocyanoethoxy) dioxane, bis(b -thiocyanoethoxy) methane, a -a -bis(b -thiocyano-ethoxy) ethane, a -a -bis (b  - thiocyano - ethoxy) - b  - methyl propane, a -a -bis(b  - thiocyanoethoxy)butane, a -a -bis(b  - thiocyano - ethoxy) heptane, a -a -bis(b  - thiocyano - ethoxy)g  - thiocyano propane, a -a -bis(b  - thiocyano - ethoxy) butene 2, bis(g -thiocyano-propoxy)methane, a -a -bis(g -thiocyano - propoxy) - b  - methyl propane, tris(b  - thiocyano - ethyl)amine, and bis(b -thiocyano-ethyl) sulphide.  The Specification as open to inspection under Sect. 91 is not limited to aliphatic compounds of the kind described above, and includes an example for the production of bis(b -thiocyano-ethoxy) phenyl methane, and includes also the production of the esters described in Specification 478,604.  This subject-matter does not appear in the Specification as accepted.