GB1336323A - Herbicidal ureas their production their use and compositions containing them - Google Patents
Herbicidal ureas their production their use and compositions containing themInfo
- Publication number
- GB1336323A GB1336323A GB2464971*A GB2464971A GB1336323A GB 1336323 A GB1336323 A GB 1336323A GB 2464971 A GB2464971 A GB 2464971A GB 1336323 A GB1336323 A GB 1336323A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- prepared
- alkyl radical
- compound
- oxadiazoles
- 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
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1336323 Oxadiazoles and thiadiazoles AGRIPAT SA 19 April 1971 [19 March 1970] 24649/71 Heading C2C [Also in Division A5] Compounds of formula wherein R 1 is an α-halo-C 1-6 -alkyl radical, containing 1 to 3 halogen atoms attached to the α-carbon atom, each of R 2 and R 3 is hydrogen or a C 1-6 alkyl radical, R 4 is a C 1-6 alkyl radical optionally substituted by a cyano or C 1-4 - alkoxy group, or is a C 3-10 cycloalkyl, (C 1-6 - alkyl)-C 3-10 -cycloalkyl, alkenyl, haloalkenyl or alkynyl group and X is oxygen or sulphur, are prepared by (a) reaction of a 3-R 1 -5-aminooxadiazole or thiadiazole with a halocarbonic or halothiocarbonic ester or with phosgene to give a carbamate or thiocarbamate ester or carbamic acid halide and reacting this with an amine, or (b) reaction of a 3-R 1 -5-amino-oxadiazole or thiadiazole with an isocyanate or an N-substituted carbamic acid halide. The products are herbicides. 3 - R 1 - 5 - Amino - oxadiazoles and thiadiazoles are prepared by (a) reaction of a trihaloacetamidoxime, with cyanogen bromide, (b) reaction of a 5-trichloromethyl-compound with ammonia or (c) conversion of a 3-trihalomethyl compound to a 3-dihalomethyl compound by catalytic hydrogenation. 3 - Trifluoromethyl - 5 - trichloromethyl - 1,2,4- oxadiazole is prepared by reaction of 2,2,2-trifluoro-acetamidoxime with trichloroacetic anhydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH415970A CH549338A (en) | 1970-03-19 | 1970-03-19 | HERBICIDAL AGENT. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1336323A true GB1336323A (en) | 1973-11-07 |
Family
ID=4270900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2464971*A Expired GB1336323A (en) | 1970-03-19 | 1971-04-19 | Herbicidal ureas their production their use and compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5439447B1 (en) |
| AT (1) | AT304158B (en) |
| AU (1) | AU2666771A (en) |
| BE (1) | BE764448A (en) |
| BG (1) | BG17709A3 (en) |
| CA (1) | CA962274A (en) |
| CH (1) | CH549338A (en) |
| DE (1) | DE2113033A1 (en) |
| ES (1) | ES389361A1 (en) |
| FR (1) | FR2084809A5 (en) |
| GB (1) | GB1336323A (en) |
| IL (1) | IL36439A (en) |
| NL (1) | NL168223C (en) |
| OA (1) | OA03617A (en) |
| RO (1) | RO58063A (en) |
| SU (1) | SU388381A3 (en) |
| ZA (1) | ZA711784B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3019259A1 (en) * | 1979-05-23 | 1980-12-04 | Ciba Geigy Ag | SALTS OF HERBICIDES 1,2,4-THIADIAZOLYL-5-UREA DERIVATIVES AND THEIR USE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670924B2 (en) * | 1967-09-19 | 1976-11-18 | Bayer Ag, 5090 Leverkusen | 1,2,4-THIADIAZOLYL UREA DERIVATIVES |
-
1970
- 1970-03-19 CH CH415970A patent/CH549338A/en not_active IP Right Cessation
-
1971
- 1971-03-10 BG BG017005A patent/BG17709A3/en unknown
- 1971-03-16 OA OA54199A patent/OA03617A/en unknown
- 1971-03-18 AT AT233571A patent/AT304158B/en not_active IP Right Cessation
- 1971-03-18 CA CA108,079A patent/CA962274A/en not_active Expired
- 1971-03-18 ZA ZA711784A patent/ZA711784B/en unknown
- 1971-03-18 RO RO66311A patent/RO58063A/ro unknown
- 1971-03-18 NL NLAANVRAGE7103671,A patent/NL168223C/en not_active IP Right Cessation
- 1971-03-18 AU AU26667/71A patent/AU2666771A/en not_active Expired
- 1971-03-18 IL IL36439A patent/IL36439A/en unknown
- 1971-03-18 JP JP1501771A patent/JPS5439447B1/ja active Pending
- 1971-03-18 FR FR7109501A patent/FR2084809A5/fr not_active Expired
- 1971-03-18 DE DE19712113033 patent/DE2113033A1/en not_active Withdrawn
- 1971-03-18 BE BE764448A patent/BE764448A/en unknown
- 1971-03-18 ES ES0389361A patent/ES389361A1/en not_active Expired
- 1971-03-19 SU SU1635867A patent/SU388381A3/ru active
- 1971-04-19 GB GB2464971*A patent/GB1336323A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2113033A1 (en) | 1971-09-30 |
| FR2084809A5 (en) | 1971-12-17 |
| IL36439A0 (en) | 1971-05-26 |
| RO58063A (en) | 1975-06-15 |
| NL168223B (en) | 1981-10-16 |
| ZA711784B (en) | 1971-12-29 |
| BG17709A3 (en) | 1973-12-25 |
| NL7103671A (en) | 1971-09-21 |
| BE764448A (en) | 1971-09-20 |
| CH549338A (en) | 1974-05-31 |
| ES389361A1 (en) | 1973-05-01 |
| AU2666771A (en) | 1972-09-02 |
| SU388381A3 (en) | 1973-06-22 |
| OA03617A (en) | 1971-03-30 |
| JPS5439447B1 (en) | 1979-11-28 |
| AT304158B (en) | 1972-12-27 |
| IL36439A (en) | 1974-03-14 |
| NL168223C (en) | 1982-03-16 |
| CA962274A (en) | 1975-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |