GB1008266A - 3-substituted benzoxazine-(1,4)-one-(2) derivatives - Google Patents
3-substituted benzoxazine-(1,4)-one-(2) derivativesInfo
- Publication number
- GB1008266A GB1008266A GB502563A GB502563A GB1008266A GB 1008266 A GB1008266 A GB 1008266A GB 502563 A GB502563 A GB 502563A GB 502563 A GB502563 A GB 502563A GB 1008266 A GB1008266 A GB 1008266A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- aryl
- alkyl
- aralkyl
- benzoxazine
- 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
- -1 C1-C4 alkyl radical Chemical group 0.000 abstract 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- WHHYMBKESAOOSX-UHFFFAOYSA-N 1,3-benzoxazole-2-carboxamide Chemical class C1=CC=C2OC(C(=O)N)=NC2=C1 WHHYMBKESAOOSX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- FOGYJXIJOUAEAZ-UHFFFAOYSA-N 3-chloro-2H-1,2-benzoxazine Chemical compound C1=CC=C2ONC(Cl)=CC2=C1 FOGYJXIJOUAEAZ-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 abstract 1
- 238000009472 formulation Methods 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
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000004237 preparative chromatography Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 abstract 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 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 compounds of the general formula <FORM:1008266/C2/1> wherein R is a chlorine atom or a C1-C4 alkyl radical, n represents O or an integer of 1 to 4 and X represents an ammonium, cyclimmonium or phosphonium radical or a -SH, -O-CO-R1, -S-CO-R1, -O-CS-R1, -S-CS-R1, -S-CS-OR1, -NR211, -O-CO-NR211, -O-CS-NR211 or -S-CS-NR211, wherein R1 is an alkyl, aryl, aralkyl or cycloalkyl radical and R11 is a hydrogen atom or an alkyl, aryl, aralkyl or cycloalkyl radical or an aryl radical containing 1-3 chlorine atoms or NR211 represents a heterocyclic radical. These 3-substituted benzoxazine-(1,4)-one-(2) derivative may be produced by reacting a 3-chloro-benzoxazine - (1,4) - one - (2) of the formula <FORM:1008266/C2/2> with ammonia, an amine, phosphine, hydrogen sulphide, or an alkali metal, alkaline earth metal or ammonium salt of a carboxylic, thiocarboxylic, xanthogenic, carbamic or thiocarbamic acid. The reaction is expediently performed in an inert organic solvent or diluent at - 30 DEG to + 200 DEG C., preferably - 20 DEG to + 60 DEG C., and, when employing ammonia or an amine as reactant, an excess thereof may be used as an acid-binding agent. Benzoxazole-2-carboxylic acid amides, formed as by-products in the above reaction when ammonia or a strongly basic primary or secondary amine is employed, may be separated from the compounds of the invention by, for example, fractional crystallisation or preparative chromatography. Some of said amides are described and claimed in Specification 1,008,267.ALSO:Herbicidal compositions contain one or more compounds of the general formula <FORM:1008266/A5-A6/1> wherein R is a chloric atom or a C1-C4 alkyl radical, n is 0 or an integer of 1 to 4 and X represents an ammonium, cyclimmonium or phosphonium radical or a -SH, -O-CO-R1, -S-CO-R1, -O-CS-R1, -S-CS-R1, -S-CS-OR1, -NR112, -OCONR112, -O-CS-NR112 or -S-CS-NR112 radical wherein R1 is an alkyl, aryl, aralkyl or cycloalkyl radical and R11 is a hydrogen atom or an alkyl, aryl, aralkyl, or cycloalkyl radical or an aryl radical containing 1 to 3 chlorine atoms or R112 may represent a heterocyclic radical, and a solid or liquid diluent or carrier. The compositions may also contain, as active ingredients, known herbicides or benzoxazole-2-carboxylic acid amides of the formula <FORM:1008266/A5-A6/2> which amides may be formed as by-products in the preparation of the 3-substituted benzoxazine-(1,4)-one-(2) derivatives. Emulsifying and dispersing agents may also be present and the compositions may be applied as emulsifiable concentrates, spray powders, pastes, soluble powders, dusts and granulates. Said formulations contain the benzoxazine-(1, 4)-ones in amounts between 0.1 and 95% by weight. Specification 1,008,267 is referred to.
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 |
|---|---|
| GB1008266A true GB1008266A (en) | 1965-10-27 |
Family
ID=7096252
Family Applications (2)
| 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 |
| GB3858364A Expired GB1008267A (en) | 1962-02-07 | 1963-02-07 | Benzoxazole-2-carboxylic acid derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3858364A Expired GB1008267A (en) | 1962-02-07 | 1963-02-07 | Benzoxazole-2-carboxylic acid derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1197677B (en) |
| GB (2) | GB1008266A (en) |
| NL (1) | NL288637A (en) |
Families Citing this family (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 GB502563A patent/GB1008266A/en not_active Expired
- 1963-02-07 GB GB3858364A patent/GB1008267A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL288637A (en) | |
| DE1197677B (en) | 1965-07-29 |
| GB1008267A (en) | 1965-10-27 |
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