GB1036075A - Improvements in or relating to 4-imino-oxazolidin-2-ones - Google Patents
Improvements in or relating to 4-imino-oxazolidin-2-onesInfo
- Publication number
- GB1036075A GB1036075A GB739464A GB739464A GB1036075A GB 1036075 A GB1036075 A GB 1036075A GB 739464 A GB739464 A GB 739464A GB 739464 A GB739464 A GB 739464A GB 1036075 A GB1036075 A GB 1036075A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxazolidin
- imino
- formula
- ones
- chloroaryl
- 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
- CVKQGYLUHQGQJF-UHFFFAOYSA-N 4-amino-5h-1,3-oxazol-2-one Chemical class N=C1COC(=O)N1 CVKQGYLUHQGQJF-UHFFFAOYSA-N 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 alkyl radical Chemical class 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- KQQARNJXAAMXMR-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-imino-5-methyl-1,3-oxazolidin-2-one Chemical compound ClC1=CC=C(C=C1)N1C(OC(C1=N)C)=O KQQARNJXAAMXMR-UHFFFAOYSA-N 0.000 abstract 1
- DJIVQZMWHIIYMW-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-ethyl-1,3-oxazolidine-2,4-dione Chemical compound ClC1=CC=C(C=C1)N1C(OC(C1=O)CC)=O DJIVQZMWHIIYMW-UHFFFAOYSA-N 0.000 abstract 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000001475 oxazolidinediones Chemical class 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Novel 4 - imino - oxazolidin - 2 - ones of the formula <FORM:1036075/C2/1> wherein Y represents an alkyl or aryl radical (including chloroaryl) and R1 and R2 represent hydrogen or a straight or branched alkyl radical and salts thereof, are prepared by isomerizing a urethane-nitrile of the formula <FORM:1036075/C2/2> with an alkaline catalyst and, if desired, further reacting the product with an acid to form a salt. The urethane-nitrile starting material may be prepared in situ from an isocyanate YNCO and a cyanhydrin of the formula <FORM:1036075/C2/3> The 4 - imino - oxazolidin - 2 - ones may be N-brominated by treatment with chloroform solutions of bromine, hydrolysed under neutral or alkaline conditions to give compounds in which the oxazole ring is cleared (e.g. CIC6H4NHCO.CH(OH)CH3 from 3 - para - chlorophenyl - 5 - methyl - 4 - imino - oxazolidin - 2 - one), or hydrolysed under acid conditions to yield corresponding oxazolidinediones (e.g. 3 - para - chlorophenyl-5-ethyl-oxazolidine-2,4-dione).ALSO:Herbicidal compositions contain as the active ingredient a 4-ineiro-oxazoldin-2-one of the formula:- <FORM:1036075/A5-A6/1> or a salt thereof, wherein Y represents an alkyl or aryl radical (including chloroaryl) and R1 and R2 represent hydrogen or a straight or branched alkyl radical. The compositions may be in the form of a powder, a solution in an organic solvent or an emulsion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR927237A FR1506257A (en) | 1963-03-08 | 1963-03-08 | Imino-4 oxazolidinones-2 and method of preparation |
| FR927238A FR1358627A (en) | 1963-03-08 | 1963-03-08 | Method of regulating plant growth using imino-4 oxazolidinones-2 and urethanes nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1036075A true GB1036075A (en) | 1966-07-13 |
Family
ID=26200148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB739464A Expired GB1036075A (en) | 1963-03-08 | 1964-02-21 | Improvements in or relating to 4-imino-oxazolidin-2-ones |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE644178A (en) |
| CH (1) | CH444161A (en) |
| DE (1) | DE1445696A1 (en) |
| FR (2) | FR1506257A (en) |
| GB (1) | GB1036075A (en) |
| LU (1) | LU45542A1 (en) |
| NL (1) | NL148891B (en) |
-
1963
- 1963-03-08 FR FR927237A patent/FR1506257A/en not_active Expired
- 1963-03-08 FR FR927238A patent/FR1358627A/en not_active Expired
-
1964
- 1964-02-21 GB GB739464A patent/GB1036075A/en not_active Expired
- 1964-02-21 BE BE644178D patent/BE644178A/xx unknown
- 1964-02-27 CH CH244164A patent/CH444161A/en unknown
- 1964-02-27 LU LU45542A patent/LU45542A1/xx unknown
- 1964-03-04 DE DE19641445696 patent/DE1445696A1/en active Pending
- 1964-03-09 NL NL6402418A patent/NL148891B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL148891B (en) | 1976-03-15 |
| LU45542A1 (en) | 1964-04-27 |
| FR1358627A (en) | 1964-04-17 |
| DE1445696A1 (en) | 1969-05-14 |
| FR1506257A (en) | 1967-12-22 |
| NL6402418A (en) | 1964-09-09 |
| CH444161A (en) | 1967-09-30 |
| BE644178A (en) | 1964-06-15 |
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