ES361837A1 - New 1,3,4-thiadiazolyl ureas - Google Patents
New 1,3,4-thiadiazolyl ureasInfo
- Publication number
- ES361837A1 ES361837A1 ES361837A ES361837A ES361837A1 ES 361837 A1 ES361837 A1 ES 361837A1 ES 361837 A ES361837 A ES 361837A ES 361837 A ES361837 A ES 361837A ES 361837 A1 ES361837 A1 ES 361837A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- radical
- formula
- acid
- reaction
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the general formula wherein R 1 represents a perfluoroalkyl radical with 1 or 2 carbon atoms, R 2 represents hydrogen or an alkyi radical having. to 4 carbon atoms, R 3 represents hydrogen or an alkyl radical having 1 to 4 carbon atoms with the proviso that at least one of the symbols R 2 and R 3 represents hydrogen, and R 4 represents an alkyl radical having 1 to 4 carbon atoms which is unsubstituted or is substituted by a substituent selected from chlorine, bromine, cyano, alkoxy having 1 to 3 carbon atoms, alkyl thio having 1 to 3 carbon atoms an alkenyl or alkynyl radical with 3 or 4 carbon atoms, a cycloalkyl radical with 3 to 6 carbon atoms, or. an alkoxy radical having 1 to 3 carbon atoms. The compounds may be prepared from amines of the general formula by (i) reaction with a haloformic acid ester or halothioformic acid s-ester in the presence of an acid-binding agent to form the corresponding carbamate or thiocarbamate which is reacted with an amine of the formula R 3 R 4 NH, (ii) reaction with an isocyanate of the formula R 4 -NCO where R 4 is as defined above except that it may not represent cyanoalkyl, alkenyl, alkynyl or alkoxy, (iii) when R 2 = H, reaction with a compound of the formula R 3 R 4 N-CO-halogen in the presence of an acid-binding: agent, R 3 being C 1-4 alkyl, (iv) reaction with COCl 2 to give the carbamoyl chloride which is then reacted with an amine R 3 R 4 NH. Aminothiadiazoles of the Formula II above are obtained by ring-closure with polyphosphoric acid fluoroacyl -thioaemicarbazides of the formula R 1 CONHNHCSNHR 2 which are themselves obtained by acylation of the appropriate thiosemicarbazide with a fluorocarboxylic acid derivative, e.g. the anhydride. The compounds of the invention display herbi- cidal activity and may be formulated with conventional additives, fertilizers, or other known herbicides.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1820667A CH488723A (en) | 1967-12-27 | 1967-12-27 | Process for the production of thiadiazolyl ureas |
| CH1520568A CH503757A (en) | 1967-12-27 | 1968-10-11 | Process for the production of thiadiazolyl ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES361837A1 true ES361837A1 (en) | 1970-11-16 |
Family
ID=25715932
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES361839A Expired ES361839A1 (en) | 1967-12-27 | 1968-12-23 | New 1,3,4-thiadiazolyl ureas |
| ES361838A Expired ES361838A1 (en) | 1967-12-27 | 1968-12-24 | New 1,3,4-thiadiazolyl ureas |
| ES361837A Expired ES361837A1 (en) | 1967-12-27 | 1968-12-24 | New 1,3,4-thiadiazolyl ureas |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES361839A Expired ES361839A1 (en) | 1967-12-27 | 1968-12-23 | New 1,3,4-thiadiazolyl ureas |
| ES361838A Expired ES361838A1 (en) | 1967-12-27 | 1968-12-24 | New 1,3,4-thiadiazolyl ureas |
Country Status (13)
| Country | Link |
|---|---|
| AT (3) | AT291282B (en) |
| BE (1) | BE725984A (en) |
| BG (3) | BG15577A3 (en) |
| CH (2) | CH488723A (en) |
| CS (1) | CS157650B2 (en) |
| DE (1) | DE1816696C2 (en) |
| DK (1) | DK122728B (en) |
| ES (3) | ES361839A1 (en) |
| FR (1) | FR1601517A (en) |
| GB (1) | GB1254468A (en) |
| IL (1) | IL31333A (en) |
| MY (1) | MY7500074A (en) |
| NL (1) | NL139172B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757655A (en) * | 1969-10-17 | 1971-04-16 | Air Prod & Chem | PESTICIDES FOR AGRICULTURAL USE |
| CA931961A (en) * | 1970-04-17 | 1973-08-14 | Gulf Research And Development Company | Combating unwanted vegetation with 1,3,4-thiadiazolylureas |
| DE2059328C2 (en) * | 1970-11-24 | 1984-02-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3- (5-ethylsulfinyl-1,3,4-thiadiazol-2-YL) urea |
| DE2330453A1 (en) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| US3990881A (en) * | 1975-08-25 | 1976-11-09 | Eli Lilly And Company | 5-(Hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas |
| GB1561636A (en) * | 1975-11-07 | 1980-02-27 | Lilly Industries Ltd | Herbicidal combinations |
| US4271166A (en) * | 1977-08-15 | 1981-06-02 | Eli Lilly And Company | N-(1,3,4-Thiadiazol-2-yl)benzamides |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
| US4987233A (en) * | 1988-06-15 | 1991-01-22 | Eli Lilly And Company | Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives |
| JP5527923B2 (en) * | 2007-03-28 | 2014-06-25 | 公益財団法人相模中央化学研究所 | Heterocyclic compound having perfluoroalkyl group and method for producing the same |
| CN109053634A (en) * | 2018-09-26 | 2018-12-21 | 河北工业大学 | A kind of preparation method of thiazfluron raw medicine |
| CN111218200B (en) * | 2020-01-17 | 2022-03-01 | 北京信为兢创科技有限公司 | High-wear-resistance moisture-proof coating composition and preparation method and application thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655445A (en) * | 1949-12-06 | 1953-10-13 | Du Pont | 3-(halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |
| DE964548C (en) * | 1955-06-03 | 1957-05-23 | Bayer Ag | Herbicides |
| DE1028986B (en) * | 1956-01-17 | 1958-04-30 | Hoechst Ag | Process for the production of new urea derivatives |
| DE1770467U (en) | 1956-12-18 | 1958-07-17 | Bremshey & Co | CONNECTORS FOR THE PARTS OF DECORATIVE FRAMES. |
| BE594227A (en) * | 1959-08-21 | |||
| CH403391A (en) * | 1960-11-22 | 1965-11-30 | Ciba Geigy | Herbicidal agent containing new ureas |
| CH398543A (en) * | 1961-05-06 | 1966-03-15 | Ciba Geigy | Process for the production of urea derivatives |
| DE1901672U (en) | 1962-02-22 | 1964-10-01 | Walter Hebel | CLAMPING PLATE. |
| BE632848A (en) * | 1962-05-28 | |||
| OA01933A (en) * | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Thiazole derivatives. |
| DE1542789C3 (en) * | 1965-09-18 | 1978-05-18 | Bayer Ag, 5090 Leverkusen | Selective weed control |
-
1967
- 1967-12-27 CH CH1820667A patent/CH488723A/en not_active IP Right Cessation
-
1968
- 1968-10-11 CH CH1520568A patent/CH503757A/en not_active IP Right Cessation
- 1968-12-20 DK DK628068AA patent/DK122728B/en not_active IP Right Cessation
- 1968-12-23 AT AT305070A patent/AT291282B/en not_active IP Right Cessation
- 1968-12-23 GB GB60940/68A patent/GB1254468A/en not_active Expired
- 1968-12-23 AT AT305170A patent/AT291670B/en not_active IP Right Cessation
- 1968-12-23 ES ES361839A patent/ES361839A1/en not_active Expired
- 1968-12-23 AT AT1249468A patent/AT291276B/en active
- 1968-12-23 DE DE1816696A patent/DE1816696C2/en not_active Expired
- 1968-12-24 NL NL686818641A patent/NL139172B/en not_active IP Right Cessation
- 1968-12-24 ES ES361838A patent/ES361838A1/en not_active Expired
- 1968-12-24 ES ES361837A patent/ES361837A1/en not_active Expired
- 1968-12-24 BE BE725984D patent/BE725984A/xx not_active IP Right Cessation
- 1968-12-26 IL IL31333A patent/IL31333A/en unknown
- 1968-12-26 BG BG011317A patent/BG15577A3/en unknown
- 1968-12-26 FR FR1601517D patent/FR1601517A/fr not_active Expired
- 1968-12-26 BG BG013638A patent/BG15579A3/en unknown
- 1968-12-27 CS CS882468A patent/CS157650B2/cs unknown
-
1969
- 1969-04-16 BG BG012072A patent/BG15522A3/en unknown
-
1975
- 1975-12-30 MY MY74/75A patent/MY7500074A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT291282B (en) | 1971-07-12 |
| ES361839A1 (en) | 1971-01-01 |
| IL31333A0 (en) | 1969-02-27 |
| CS157650B2 (en) | 1974-09-16 |
| BE725984A (en) | 1969-06-24 |
| AT291670B (en) | 1971-07-26 |
| GB1254468A (en) | 1971-11-24 |
| FR1601517A (en) | 1970-08-24 |
| CH503757A (en) | 1971-02-28 |
| NL139172B (en) | 1973-06-15 |
| AT291276B (en) | 1971-07-12 |
| BG15579A3 (en) | 1972-05-20 |
| BG15522A3 (en) | 1976-06-21 |
| IL31333A (en) | 1972-07-26 |
| MY7500074A (en) | 1975-12-31 |
| NL6818641A (en) | 1969-07-01 |
| DE1816696A1 (en) | 1969-08-21 |
| CH488723A (en) | 1970-04-15 |
| DE1816696C2 (en) | 1983-05-19 |
| DK122728B (en) | 1972-04-04 |
| BG15577A3 (en) | 1972-05-20 |
| ES361838A1 (en) | 1970-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19840914 |