GB1008267A - Benzoxazole-2-carboxylic acid derivatives - Google Patents
Benzoxazole-2-carboxylic acid derivativesInfo
- Publication number
- GB1008267A GB1008267A GB3858364A GB3858364A GB1008267A GB 1008267 A GB1008267 A GB 1008267A GB 3858364 A GB3858364 A GB 3858364A GB 3858364 A GB3858364 A GB 3858364A GB 1008267 A GB1008267 A GB 1008267A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aralkyl
- radical
- cycloalkyl
- general formula
- 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
- VKPJOERCBNIOLN-UHFFFAOYSA-N 1,3-benzoxazole-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=NC2=C1 VKPJOERCBNIOLN-UHFFFAOYSA-N 0.000 title abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 239000011230 binding agent Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000004237 preparative chromatography Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000007921 spray 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
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
- C07F9/65335—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises benzoxazole-2-carboxylic acid derivatives of the general formula <FORM:1008267/C2/1> wherein R represents a chlorine atom or an alkyl radical containing 1 to 4 carbon atoms, n is O or an integer of 1 to 4, and Y represents -OR1 or -NR112, wherein R1 represents an alkyl, aralkyl, cycloalkyl, aryl or chloroaryl radical and R11 represents a hydrogen atom or an alkyl, aralkyl or cycloalkyl radical, or -NR112 represents a heterocyclic ring. They may be prepared by causing a 3-chlorobenzoxazine-(1,4)-one-(2) of the general formula <FORM:1008267/C2/2> to react with ammonia, a strong basic primary or secondary amine, an alcohol, a phenol or a chlorophenol in the presence of an acid binding agent. The reaction is expediently performed in an inert organic solvent or diluent at -30 DEG to + 200 DEG C. and when one of the reactants is an alcohol it can advantageously be used in excess as the diluent. Specified acid binding agents are the alkali metal and alkaline earth metal hydroxides, carbonates and bicarbonates, but in the case of the reaction with ammonia or an amine an excess thereof can be used instead of the binding agent. The compounds of the invention may be isolated from the reaction mixture, which may contain the corresponding 3-substituted-benzoxazine-(1,4)-ones-(2) as by-products (see Specification 1,008,266), by, for example, fractional crystallization or preparative chromatography.ALSO:Herbicidal compositions comprise benzoxazole-2-carboxylic acid derivatives of the general formula <FORM:1008267/A5-A6/1> wherein R represents a chloric atom or an alkyl radical containing 1 to 4 carbon atoms, n is 0 or an integer of 1 to 4, and 7 represents -OR1 or -NR112, wherein R1 represents an alkyl, aralkyl, cycloalkyl, aryl or chloroaryl radical and R11 represents a hydrogen atom or an alkyl, aralkyl or cycloalkyl radical, or -NR112 represents a heterocyclic ring. The compositions may be in the form of p emulsifiable concentrates, spray powders, pastes, soluble powders, dusts or granulates and contain 0.1 to 95% by weight of the active compounds. Alternatively these compounds may be employed alone or as a mixture with the corresponding 3-substituted-benzoxazine-(1, 4)-ones-(2) (see Specification 1,008,266).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35959A DE1197677B (en) | 1962-02-07 | 1962-02-07 | Selective herbicidal agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008267A true GB1008267A (en) | 1965-10-27 |
Family
ID=7096252
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3858364A Expired GB1008267A (en) | 1962-02-07 | 1963-02-07 | Benzoxazole-2-carboxylic acid derivatives |
| GB502563A Expired GB1008266A (en) | 1962-02-07 | 1963-02-07 | 3-substituted benzoxazine-(1,4)-one-(2) derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB502563A Expired GB1008266A (en) | 1962-02-07 | 1963-02-07 | 3-substituted benzoxazine-(1,4)-one-(2) derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1197677B (en) |
| GB (2) | GB1008267A (en) |
| NL (1) | NL288637A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4620010A (en) * | 1984-03-29 | 1986-10-28 | Usv Pharmaceutical Corp. | Process for preparing carboalkoxy substituted benzoxazole compounds |
-
0
- NL NL288637D patent/NL288637A/xx unknown
-
1962
- 1962-02-07 DE DEF35959A patent/DE1197677B/en active Pending
-
1963
- 1963-02-07 GB GB3858364A patent/GB1008267A/en not_active Expired
- 1963-02-07 GB GB502563A patent/GB1008266A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4620010A (en) * | 1984-03-29 | 1986-10-28 | Usv Pharmaceutical Corp. | Process for preparing carboalkoxy substituted benzoxazole compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL288637A (en) | |
| GB1008266A (en) | 1965-10-27 |
| DE1197677B (en) | 1965-07-29 |
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