ES368447A1 - Halo substituted uracils and hydrouracils and preparation of same - Google Patents
Halo substituted uracils and hydrouracils and preparation of sameInfo
- Publication number
- ES368447A1 ES368447A1 ES368447A ES368447A ES368447A1 ES 368447 A1 ES368447 A1 ES 368447A1 ES 368447 A ES368447 A ES 368447A ES 368447 A ES368447 A ES 368447A ES 368447 A1 ES368447 A1 ES 368447A1
- Authority
- ES
- Spain
- Prior art keywords
- alkoxy
- alkyl
- halogen
- halo
- uracil
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Abstract
Compounds of formul[mu] wherein X is halogen or C 1 _ 4 alkyl, Y is halogen, R 1 is halogen, hydroxy, C 1 _ 6 alkoxy or mono- or dihalo- C 1 _ 6 alkoxy, R 2 is hydrogen, C 1 _ 6 alkyl optionally substituted by halogen, hydroxy or C 1 _ 4 alkoxy groups, C 2 _ 6 alkenyl, cyclohexyl, or phenyl optionally substituted by nitro, halogen, C 1 _ 4 alkoxy, mono- or di halo- C 1 _ 4 alkoxy or trifluoromethyl groups, R 3 is hydrogen C 1 _ 4 alkyl, halo, C 1 _ 4 alkoxy, cyano, thiocyano, nitro or C 1 _ 4 alkylthio and R 4 is or optionally substituted C 1 _ 12 alkyl, C 2 _ 6 alkenyl C 3 _ 8 cycloalkyl, phenyl or benzyl, the substituents being selected from halo, nitro, amino, C 1 _ 4 alkyl, halo- C 1 _ 4 alkyl, C 1 _ 4 alkoxy, carboxy or carb-C 1 _ 4 - alkoxy groups, and water-soluble salts thereof, are prepared by (a) formation of a uracil wherein R 3 is hydrogen by reaction of'a compound of formula CF 3 C(NH 2 ) = CR 3 COOR 5 , wherein R 5 is. C 1 _ 4 alkyl, with an isocyanate R 4 NCO, (b) introduction of a substituent R 3 by known methods, or (c) , conversion of a uracil to a hydrouracil by reaction with halogen inthe presence of water or a C 1 _ 6 alkanol or haloalkanol, followed optionally by replacement of a hydroxy substituent R 1 by a halogen atom. Alkoxy substituents R 3 in uracils may be introduced by reaction of a compound CF 3 C(NH 2 )= CHCOOR 5 with an isothiocyanate R 4 NCS to form a thiouracil, reacting this with bromine to form a 2,21- dithiobis - (5 - bromo - 4 - pyrimidone), treating this with a sodium alkoxide and zinc dust to form a 5 - alkoxy - 2 - thiouracil and treating this with chloroacetic and to form a 5-alkoxy-uracil. The products have, herbicidal activity. 5 - Bromo - 6 - trifluoromethyl - uracil is prepared by bromination.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73728868A | 1968-06-17 | 1968-06-17 | |
US73730868A | 1968-06-17 | 1968-06-17 | |
US80470869A | 1969-03-05 | 1969-03-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES368447A1 true ES368447A1 (en) | 1971-05-01 |
Family
ID=27419225
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES368447A Expired ES368447A1 (en) | 1968-06-17 | 1969-06-17 | Halo substituted uracils and hydrouracils and preparation of same |
ES370564A Expired ES370564A1 (en) | 1968-06-17 | 1969-08-16 | Halo substituted uracils and hydrouracils and preparation of same |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES370564A Expired ES370564A1 (en) | 1968-06-17 | 1969-08-16 | Halo substituted uracils and hydrouracils and preparation of same |
Country Status (10)
Country | Link |
---|---|
BE (1) | BE742508A (en) |
CH (1) | CH523259A (en) |
DE (1) | DE1930776A1 (en) |
DK (1) | DK132682C (en) |
ES (2) | ES368447A1 (en) |
FR (1) | FR2011113A1 (en) |
GB (1) | GB1240392A (en) |
IL (1) | IL32279A (en) |
NL (1) | NL6909144A (en) |
SE (1) | SE379043B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0338686B1 (en) * | 1988-04-22 | 1994-06-22 | Zeneca Limited | Pyrimidinone derivatives |
GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
TWI643623B (en) | 2011-10-03 | 2018-12-11 | 菲瑞茵公司 | Composition for the treatment of fistula |
-
1969
- 1969-05-22 IL IL32279A patent/IL32279A/en unknown
- 1969-05-28 GB GB27119/69A patent/GB1240392A/en not_active Expired
- 1969-06-10 SE SE6908240A patent/SE379043B/xx unknown
- 1969-06-16 NL NL6909144A patent/NL6909144A/xx unknown
- 1969-06-16 DK DK322169A patent/DK132682C/en active
- 1969-06-17 CH CH924669A patent/CH523259A/en not_active IP Right Cessation
- 1969-06-17 FR FR6920192A patent/FR2011113A1/fr not_active Withdrawn
- 1969-06-17 ES ES368447A patent/ES368447A1/en not_active Expired
- 1969-06-18 DE DE19691930776 patent/DE1930776A1/en active Pending
- 1969-08-16 ES ES370564A patent/ES370564A1/en not_active Expired
- 1969-12-02 BE BE742508D patent/BE742508A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK132682C (en) | 1976-06-28 |
SE379043B (en) | 1975-09-22 |
CH523259A (en) | 1972-05-31 |
DK132682B (en) | 1976-01-26 |
BE742508A (en) | 1970-06-02 |
NL6909144A (en) | 1969-12-19 |
ES370564A1 (en) | 1971-04-16 |
IL32279A0 (en) | 1969-07-30 |
IL32279A (en) | 1973-01-30 |
GB1240392A (en) | 1971-07-21 |
FR2011113A1 (en) | 1970-02-27 |
DE1930776A1 (en) | 1970-01-02 |
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