ES370564A1 - Halo substituted uracils and hydrouracils and preparation of same - Google Patents

Halo substituted uracils and hydrouracils and preparation of same

Info

Publication number
ES370564A1
ES370564A1 ES370564A ES370564A ES370564A1 ES 370564 A1 ES370564 A1 ES 370564A1 ES 370564 A ES370564 A ES 370564A ES 370564 A ES370564 A ES 370564A ES 370564 A1 ES370564 A1 ES 370564A1
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
Application number
ES370564A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of ES370564A1 publication Critical patent/ES370564A1/en
Expired legal-status Critical Current

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.
ES370564A 1968-06-17 1969-08-16 Halo substituted uracils and hydrouracils and preparation of same Expired ES370564A1 (en)

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
ES370564A1 true ES370564A1 (en) 1971-04-16

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 Before (1)

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

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)

* Cited by examiner, † Cited by third party
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

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
IL32279A0 (en) 1969-07-30
IL32279A (en) 1973-01-30
ES368447A1 (en) 1971-05-01
GB1240392A (en) 1971-07-21
FR2011113A1 (en) 1970-02-27
DE1930776A1 (en) 1970-01-02

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