IL34893A - N-fluorosulphonyl compounds and their production - Google Patents
N-fluorosulphonyl compounds and their productionInfo
- Publication number
- IL34893A IL34893A IL7034893A IL3489370A IL34893A IL 34893 A IL34893 A IL 34893A IL 7034893 A IL7034893 A IL 7034893A IL 3489370 A IL3489370 A IL 3489370A IL 34893 A IL34893 A IL 34893A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- compounds
- production
- optionally substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C313/30—Y being a hetero atom
- C07C313/34—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfenylureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691943234 DE1943234A1 (en) | 1969-08-26 | 1969-08-26 | N-fluorosulfonyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34893A0 IL34893A0 (en) | 1970-09-17 |
| IL34893A true IL34893A (en) | 1973-08-29 |
Family
ID=5743752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7034893A IL34893A (en) | 1969-08-26 | 1970-07-10 | N-fluorosulphonyl compounds and their production |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE755309A (en) |
| DE (1) | DE1943234A1 (en) |
| FR (1) | FR2059292A5 (en) |
| GB (1) | GB1300796A (en) |
| IL (1) | IL34893A (en) |
| NL (1) | NL7012494A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007439B1 (en) * | 1978-07-01 | 1982-07-28 | BASF Aktiengesellschaft | Sulphamic acid halides and method for their preparation |
-
0
- BE BE755309D patent/BE755309A/xx unknown
-
1969
- 1969-08-26 DE DE19691943234 patent/DE1943234A1/en active Pending
-
1970
- 1970-07-10 IL IL7034893A patent/IL34893A/en unknown
- 1970-07-21 GB GB35184/70A patent/GB1300796A/en not_active Expired
- 1970-08-24 NL NL7012494A patent/NL7012494A/xx unknown
- 1970-08-26 FR FR7031255A patent/FR2059292A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1300796A (en) | 1972-12-20 |
| NL7012494A (en) | 1971-03-02 |
| DE1943234A1 (en) | 1971-03-04 |
| FR2059292A5 (en) | 1971-05-28 |
| IL34893A0 (en) | 1970-09-17 |
| BE755309A (en) | 1971-02-26 |
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