GB845834A - Substituted sulphonic acid amides - Google Patents
Substituted sulphonic acid amidesInfo
- Publication number
- GB845834A GB845834A GB36053/58A GB3605358A GB845834A GB 845834 A GB845834 A GB 845834A GB 36053/58 A GB36053/58 A GB 36053/58A GB 3605358 A GB3605358 A GB 3605358A GB 845834 A GB845834 A GB 845834A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acid
- aryl
- radical
- sulphonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title 1
- -1 C1-C5 alkyl radical Chemical group 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical class NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Chemical group 0.000 abstract 2
- 239000001257 hydrogen Chemical group 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 2
- OQMNWQODLIDJCA-UHFFFAOYSA-N 1-ethenylsulfonylpiperidine Chemical compound C=CS(=O)(=O)N1CCCCC1 OQMNWQODLIDJCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- TYIDPQQUJIPRBU-UHFFFAOYSA-N n-propylethenesulfonamide Chemical compound CCCNS(=O)(=O)C=C TYIDPQQUJIPRBU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds having the general formula RS-CH2-CH2-SO2-N (R1) (R2) wherein R1 is a C1-C5 alkyl radical, R2 is an alkyl radical or hydrogen or R1 and R2 together with the N atom may form a piperidino or morpholino ring, and R is an unsubstituted or substitited alkyl, aryl, or aralkyl radical, or an alkyl or aryl carboxylic acid acyl radical, an O, O dialkyl phosphoric or thiophosphonic acid acyl radical, an O-alkyl alkyl or aryl phosphonic or thiophosphonic acid acyl radical, or a dialkyl or diaryl phosphinic or thionophosphinic acid acyl radical. They may be obtained by reacting appropriate sulphydryl containing compounds (RSH) with the appropriate vinyl sulphonic acid amides (CH2=CH.SO2N(R1)(R2). Examples are given for the production of compounds of the formula: (1) <FORM:0845834/IV(b)/1> ; (2) <FORM:0845834/IV(b)/2> ; (3) <FORM:0845834/IV(b)/3> ; (4) <FORM:0845834/IV(b)/4> ; (5) <FORM:0845834/IV(b)/5> ; (6) <FORM:0845834/IV(b)/6> ; (7) <FORM:0845834/IV(b)/7> ; (8) <FORM:0845834/IV(b)/8> ; (9) <FORM:0845834/IV(b)/9> ; (10) <FORM:0845834/IV(b)/100> ; (11) <FORM:0845834/IV(b)/111> ; (12) <FORM:0845834/IV(b)/122> ; (13) <FORM:0845834/IV(b)/133> ; (14) <FORM:0845834/IV(b)/144> ; (15) <FORM:0845834/IV(b)/155> ; (16) <FORM:0845834/IV(b)/166> ; (17) <FORM:0845834/IV(b)/177> ; (18) <FORM:0845834/IV(b)/188> ; (19) <FORM:0845834/IV(b)/199> ; (20) <FORM:0845834/IV(b)/200> ; (21) <FORM:0845834/IV(b)/211> ; (22) <FORM:0845834/IV(b)/222> ; (23) <FORM:0845834/IV(b)/233> ; (24) <FORM:0845834/IV(b)/244> The products are useful as insecticides (see Group VI). The vinyl sulphonic acid amides (CH2=CH. SO2N(R1)(R2)) used as starting materials may be obtained by reacting 1 mole of a b -haloethyl sulphonic acid chloride with 3 moles of a primary or secondary amine or with 1 mole of a primary or secondary amine and 2 moles of a tertiary amine as acid binding agent. The preparation of vinyl sulphonic acid diethyl (and dimethyl) amides, vinyl sulphonic acid piperidide and vinyl sulphonic acid propyl amide are described.ALSO:An insecticidal composition comprises a solid or liquid carrier or diluent and a compound having the general formula R S. CH2.CH2.SO2. N(R1)(R2) wherein R1 is an alkyl radical containing 1 to 5 carbon atoms, R2 is alkyl or hydrogen, or R1 and R2 together with the N atom may form a piperidino or morpholino ring, and R is an unsubstituted or substituted alkyl, aryl, or aralkyl radical, or an aryl radical of either an alkyl or aryl, carboxylic acid, an O, O-dialkyl phosphoric or -thionophosphoric acid, an O- alkyl alkyl (or aryl) phosphonic or thiophosphonic acid, or of a dialkyl or diaryl phosphinic or thionophosphinic acid. Specified carriers are talc, chalk, bentonite, clay, water (if necessary with emulsifiers e.g. benzyl hydroxy diphenyl polyglycol ether), alchohols, ketones and liquid hydrocarbons. The compounds may be used in combination with each other, or with known insectisides and/or fertilizers. Specified groups (R) include phenyl, p-chlorophenyl and 2-hydroxy-ethyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE845834X | 1957-11-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB845834A true GB845834A (en) | 1960-08-24 |
Family
ID=6774901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36053/58A Expired GB845834A (en) | 1957-11-11 | 1958-11-10 | Substituted sulphonic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB845834A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259540A (en) * | 1961-02-13 | 1966-07-05 | Murphy Chemical Ltd | Stabilized insecticidal composition containing an o, o-dimethyl s-(n-alkoxymethyl) carbamoylmethyl phosphorothiolothionate |
-
1958
- 1958-11-10 GB GB36053/58A patent/GB845834A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259540A (en) * | 1961-02-13 | 1966-07-05 | Murphy Chemical Ltd | Stabilized insecticidal composition containing an o, o-dimethyl s-(n-alkoxymethyl) carbamoylmethyl phosphorothiolothionate |
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