GB900111A - Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides - Google Patents
Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicidesInfo
- Publication number
- GB900111A GB900111A GB2623459A GB2623459A GB900111A GB 900111 A GB900111 A GB 900111A GB 2623459 A GB2623459 A GB 2623459A GB 2623459 A GB2623459 A GB 2623459A GB 900111 A GB900111 A GB 900111A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoromethyl
- chloro
- sulphonyl
- aryl
- trifluoromethylbenzene
- 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
- 241000607479 Yersinia pestis Species 0.000 title abstract 3
- 239000003223 protective agent Substances 0.000 title abstract 3
- 239000004753 textile Substances 0.000 title abstract 2
- 239000004009 herbicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 2-trifluoromethyl-4-chloro-benzene-sulphonyl derivatives of 4-chloraniline Chemical class 0.000 abstract 3
- DQKPVVIVMURTDM-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1S(Cl)(=O)=O DQKPVVIVMURTDM-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 235000007319 Avena orientalis Nutrition 0.000 abstract 2
- 244000075850 Avena orientalis Species 0.000 abstract 2
- 241000219198 Brassica Species 0.000 abstract 2
- 235000003351 Brassica cretica Nutrition 0.000 abstract 2
- 235000003343 Brassica rupestris Nutrition 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 abstract 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 230000002363 herbicidal effect Effects 0.000 abstract 2
- 235000010460 mustard Nutrition 0.000 abstract 2
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 abstract 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 abstract 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 abstract 1
- CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 241000256602 Isoptera Species 0.000 abstract 1
- 244000046052 Phaseolus vulgaris Species 0.000 abstract 1
- 241001454295 Tetranychidae Species 0.000 abstract 1
- 241001454294 Tetranychus Species 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229960003280 cupric chloride Drugs 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 230000035784 germination Effects 0.000 abstract 1
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000009331 sowing Methods 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/1247—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with formation of NHSO2R or NHSO3H radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises twenty-six specific trifluoromethyl-aryl-sulphonamides, and the preparation of the compounds by reacting the appropriate trifluoromethyl - aryl-sulphochlorides with the appropriate amines. Example 1 describes the preparation of 2,21-di-trifluoromethyl-4, 41-dichloro-diphenylsulphonamide by the action of 4-chloro-2-trifluoromethylbenzene-sulphonyl chloride on 4-chloro-2-trifluoromethylaniline. In a similar way there are obtained 2-trifluoromethyl-4-chloro-benzene-sulphonyl derivatives of 4-chloraniline, 3,4-dichloraniline and 2,4,5-trichloraniline. Example 2 describes the preparation of 2-trifluoromethyl - 4 - chlorobenzene-sulphonyl-41-chlorobenzylamide by the action of 4-chloro-2-trifluoromethylbenzene-sulphonyl chloride on 4-chlorobenzylamine. Example 3 is a list of other compounds which may be similarly prepared, representative compounds being 2-chloro-5-trifluoromethylbenzenesulphonyl-di-b -chloroethylamide, 3 - trifluoromethylbenzenesulphonyl-21-trifluoromethyl -41-chloranilide, 2-fluoro - 5 - trimethylfluorobenzenesulphonyl-41-chloranilide, 5-trifluoromethyl-2-ethylsulphonylbenzenesulphonyl-41 -chloranilide, and 21,41-dichloro - 4 - trifluoromethyl - diphenylether - 2 - sulphonyl-311,411-dichloranilide. All these compounds have use as protective agents against textile pests, moulds and bacteria (see Group VIII), and have herbicidal activity (see Group VI). 4-chloro - 2 - trifluoromethylbenzene-sulphonyl-chloride is prepared by reacting 4-chloro-2-trifluorobenzene diazonium chloride with a solution of cupric chloride dissolved in aqueous acetic acid saturated with sulphur dioxide. Reference has been directed by the Comptroller to Specification 859,345.ALSO:The invention relates to novel trifluoromethyl-aryl-sulphonamides (see Group IV (b)) which have herbicidal activity, and are protective agents against pests such as termites and spider mites. In Example 6, a mixed seed of mustard and oats is sprinkled, 24 hours after sowing, with a 0.1% aqueous solution of 2-chloro - 5 - trifluoromethylbenzene - sulphonyl-21, 41, 51-trichloranilide, containing as emulsifier nonyl phenyl polyglycol ether. No germination of the mustard occurs, while the oats grow normally. Example 7 relates to the protection of bean plants against a mixed population of Tetranychus telarious by spraying the plants with 2 - chloro - 5 - trifluoromethylbenzenesulphonyl - 21 - chloro - 51 - trifluoromethyl-anilide in aqueous solution containing acetone and an emulsifier. Reference has been directed by the Comptroller to Specification 859,345.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF21888A DE1058049B (en) | 1956-12-08 | 1956-12-08 | Process for the production of protective agents against textile pests, mold and bacterial attack |
| DEF22658A DE1062238B (en) | 1957-03-23 | 1957-03-23 | Process for the production of protective agents against textile pests, mold and bacterial attack |
| DEF0026477 | 1958-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB900111A true GB900111A (en) | 1962-07-04 |
Family
ID=27210052
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3671557A Expired GB854956A (en) | 1956-12-08 | 1957-11-25 | Aromatic sulphonyl amino compounds containing trifluoromethyl radicals |
| GB2623459A Expired GB900111A (en) | 1956-12-08 | 1959-07-30 | Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3671557A Expired GB854956A (en) | 1956-12-08 | 1957-11-25 | Aromatic sulphonyl amino compounds containing trifluoromethyl radicals |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH366038A (en) |
| DE (1) | DE1418197A1 (en) |
| GB (2) | GB854956A (en) |
| SE (1) | SE303127B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322828A (en) * | 1962-12-17 | 1967-05-30 | Bayer Ag | Trifluoromethyl-sulphonic acid-trifluoromethylphenyl amides and process for their production |
| US3953492A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Anthelmintic substituted sulfonamide derivatives |
| US3953493A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Substituted sulfonamide derivatives as anthelmintic agents |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239564A (en) * | 1960-12-02 | 1966-03-08 | Reeder Earl | 2 n-substituted amino halobenzo-phenones |
-
1957
- 1957-10-30 CH CH5211357A patent/CH366038A/en unknown
- 1957-11-25 GB GB3671557A patent/GB854956A/en not_active Expired
-
1958
- 1958-08-23 DE DE19581418197 patent/DE1418197A1/en active Pending
-
1959
- 1959-06-29 CH CH7506959A patent/CH388297A/en unknown
- 1959-07-30 GB GB2623459A patent/GB900111A/en not_active Expired
- 1959-08-20 SE SE774659A patent/SE303127B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322828A (en) * | 1962-12-17 | 1967-05-30 | Bayer Ag | Trifluoromethyl-sulphonic acid-trifluoromethylphenyl amides and process for their production |
| US3953492A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Anthelmintic substituted sulfonamide derivatives |
| US3953493A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Substituted sulfonamide derivatives as anthelmintic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| SE303127B (en) | 1968-08-19 |
| GB854956A (en) | 1960-11-23 |
| CH388297A (en) | 1965-02-28 |
| CH366038A (en) | 1962-12-15 |
| DE1418197A1 (en) | 1968-10-17 |
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