IL34893A - N-fluorosulphonyl compounds and their production - Google Patents

Description

compounds and their production BAYER A 2 This invention provides new compounds of the f ormula R X I wherein R is a lower alkyl radical optionally substituted X is sulphur or is a lower alkyl optionally substituted with phenoxy optionally substituted with alkoxy or the group wherein is alkyl radical and a t The invention also provides a process the production of the novel compounds of formula ah sulphonyl fluoride of the formula R SO is in the presence of acid binding with an acyl halide formula X Hal in which Hal is fluorine and R and have same as 3 In cases where oulphamic acid fluoride and chloroformic acid phenyl ester are used as the starting the reaction follows the 0 The fluorides can be obtained by reacting n an chloride hydrofluoric The following sulphonyl fluorides among others may be used as starting materialsg n and The following are of acyl compounds suitable for in the process according to the inventions methane sulphonyl chloroacetyl chloride chloroacetyl triehloroacetyl acid process optionally carried in a reaction mixture containing an inert solvent as a diluent ethers such as diethyl ethe v and hydrocarbons such as benzene and chlorinated such as chloroform and chlorobensene0 As acid binders there may be for example tertiary nitrogen bases such as pyridines quinolineSp K or inorganic bases as alkali metal hydroxides or alkali metal V 4 e reaction dan be varied within a relatively wide although the reaction is usually carried out at a temperature of from 0 to and preferably at a temperature from 20 to Although the use of molar quantities of the starting materials s a small of up to substantially by weight either starting material is as a rule not She compounds according to the invention are valuable intermediates for further syntheses6 They can also be used themselves as insecticides shown by the test results relating to some of remaining compounds the invention possess a comparable activit test Solven 3 parts by weight of dimethyl 1 part by weight of alkylaryl pol lycol ether phenol reacted with ethylene produce a suitable active compound 1 part by weight of the active compound is mixed with the specified quantity of solvent containing the specified quantity of and the concentrate is diluted with water to the required 1 cc of the active compound preparation is appliQd with a pipette to a filter paper disc 7 cm in wet dise required Bean plants under heavy attack from bean aphids are with the active compound preparation so that the preparation penetrates into the soil without wetting the leaves of the bean The active compound absorbed by the bean plants from the soil and thus reaches the affected After the time intervals the mortality rate is determined in 100 means that all the aphids are The active their the evaluation times and the results are set out in the following TABLE Active compound Concentration of Mortality rate active compound in after 4 days in 100 5 Plutella 3 parts by weight of dimethyl 1 part by weight of alkylaryl polyglycol ether phenol reacted with ethylene To produce a suitable active compound 1 part by weight of the active compound is mixed with the specified quantity solvent containing the specified quantity of emulsifier and the concentrate is diluted with to the required Cabbage leaves are sprayed with the active compound preparation until and are then infested with caterpillars of the diamond moth After the specified time the mortality rate is determined in means that all the caterpillars are means that none are The active their the evaluation times and results set out in the following TABLE Active compounds Active compound Mortality rate concentrations in after 3 days in 100 I filtered off from the amine salt under the filtrate is concentrated and the residue A compound ing to the formulas of 62 is obtained in a yield of 89 are similarly EXAMPLE 4 11 g of triethylamine are added drop ise to a solution n of S of fluoride and 21 g acid fluoride in 150 ml of This produces a rise in temperature to After brief the reaction solution is washed with the toluene layer is dried and concenrated After a compound corresponding to the ed i yield of The starting compounds used for the process were obtained as 249 of acid chloride are added drop apparatus consisting of a 500 ml capacity pressure a condenser and an exhaust gas The reaction is then heated to 80 over period 6 hours and the hydrogen chloride formed is let off through the valve so that the internal pressure does not exceed After 153 g a compound corresponding to the S02F of 80 are obtained by fractional example Torr Torr are similarly insufficientOCRQuality

Claims (1)

1. CLAIMS compounds of the formula N X wherein R is a lower alkyl optionally substituted with X is sulphur or is a lower alkyl optionally substituted with phenoxy optionally substituted with halogenj or the group wherein is a lower alkyl radical and a I thio The compound of the formula The compound of the formula 0 The compound of the formula 0 II 12 The compound of the formula The compound of the formula compound of the formula 0 The compound the formula The compound of the formula compound of the formula 13 A process for the production of compounds according to Claim wherein an fluoride of the formula is the presence of an acid binding with an acyl halide of the formula X Hal in which Hal is fluorine or and R and have the same meanings as A process claimed in Claim wherein the reaction is conducted in the presence of an inert A process as claimed in Claim 11 or wherein the acid binding used is a tertiary nitrogen A process as claimed in any of Claims 11 to wherein the reaction is carried out at a temperature of from 0 C to preferably from to A process as claimed in any of Claims 11 to wherein the starting materials are used in molar A process for the production of pounds of Claims 1 to substantially as herein described with reference to any of the For the Apnlicants iro insufficientOCRQuality