GB1035094A - Improvements relating to herbicides and novel 3-substituted uracils - Google Patents

Improvements relating to herbicides and novel 3-substituted uracils

Info

Publication number
GB1035094A
GB1035094A GB619366A GB619366A GB1035094A GB 1035094 A GB1035094 A GB 1035094A GB 619366 A GB619366 A GB 619366A GB 619366 A GB619366 A GB 619366A GB 1035094 A GB1035094 A GB 1035094A
Authority
GB
United Kingdom
Prior art keywords
radical
carbon atoms
radical containing
substituted
cycloalkenyl
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
GB619366A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Priority claimed from US217521A external-priority patent/US3235357A/en
Priority claimed from US221890A external-priority patent/US3235358A/en
Priority claimed from US232311A external-priority patent/US3235360A/en
Priority claimed from US233952A external-priority patent/US3235361A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1035094A publication Critical patent/GB1035094A/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
    • 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
    • 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
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms

Abstract

Novel uracil addition compounds of the general formula <FORM:1035094/C2/1> or the corresponding isomeric formula <FORM:1035094/C2/2> wherein NB represents a nitrogenous base having an ionization constant Kb in water of at least 10-9; and R1, R2 and R3 are as defined in one of paragraphs (A) to (D) below:- (A) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 8 carbon atoms, an aryl radical containing 5 to 10 carbon atoms, a substituted phenyl radical, an aralkyl radical containing 5 to 13 carbon atoms, a substituted aralkyl radical containing 5 to 13 carbon atoms, an alkenyl radical containing 3 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cyano radical; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxy-methyl-thiomethyl radical; and R3 represents a methyl radical; (B) R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen atom; and R3 represents an alkyl radical containing 1 to 5 carbon atoms; (C) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, an aryl radical containing 6 to 14 carbon atoms, a substituted aryl radical containing 6 to 14 carbon atoms, an aralkyl radical containing 7 to 15 carbon atoms, a substituted aralkyl radical containing 7 to 15 carbon atoms, an alkenyl radical containing 3 to 10 carbon atoms, an alkynyl radical containing 3 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms, a cyano radical, a dialkylamino radical containing 2 to 10 carbon atoms or an alkoxy radical containing 1 to 10 carbon atoms; and R2 and R3 together represent a divalent alkylene radical of formula (CH2)n where n is 3, 4 or 5; (D) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, an aryl radical containing 5 to 14 carbon atoms, a substituted aryl radical containing 6 to 14 carbon atoms, an aralkyl radical containing 5 to 15 carbon atoms, a substituted aralkyl radical containing 5 to 15 carbon atoms, an alkenyl radical containing 3 to 10 carbon atoms, an alkynyl radical containing 3 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms, a cyano radical, a dialkylamino radical containing 2 to 10 carbon atoms, or an alkoxy radical containing 1 to 10 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine, or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; with the proviso that when R2 represents a hydrogen atom, R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; and R3 represents a hydrogen atom, are prepared by mixing equimolar amounts of the base and the uracil, if desired in a solvent. Bases used in examples are ethanolamine, octylamine, ethylenediamine, dodecylamine, cocoadiamine, piperidine, ammonia, methylamine, oleylamine, triethylamine, 2-aminooctanol-1, 2-methylpiperidine, 4-methylpiperidine, triethylenediamine, butylamine, methoxypropylamine, hexamethylenediamine, piperazine and see-butylamine. The above compounds are herbicides (see Division A5).ALSO:Uracil addition compounds of the general formula <FORM:1035094/A5-A6/1> or the corresponding isomeric formula <FORM:1035094/A5-A6/2> wherein NB represents a nitrogenous base having an ionisation constant Kb in water of at least 10-9; and R1, R2 and R3 are as defined in one of paragraphs (A) to (D) below:- (A) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 8 carbon atoms, an aryl radical containing 5 to 10 carbon atoms, a substituted phenyl radical, an aralkyl radical containing 5 to 13 carbon atoms, a substituted aralkyl radical containing 5 to 13 carbon atoms, an alkenyl radical containing 3 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cyano radical; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 4 carbon atoms; R2 represents a chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxy-methylthiomethyl radical; and R3 represents a methyl radical; (B) R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen atom; and R3 represents an alkyl radical containing 1 to 5 carbon atoms; (C) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, an aryl radical containing 6 to 14 carbon atoms, a substituted aryl radical
GB619366A 1959-08-14 1962-12-07 Improvements relating to herbicides and novel 3-substituted uracils Expired GB1035094A (en)

Applications Claiming Priority (18)

Application Number Priority Date Filing Date Title
US83370559A 1959-08-14 1959-08-14
US83370459A 1959-08-14 1959-08-14
US1296860A 1960-03-07 1960-03-07
US1296760A 1960-03-07 1960-03-07
US1295860A 1960-03-07 1960-03-07
US1295960A 1960-03-07 1960-03-07
US1295760A 1960-03-07 1960-03-07
US1295660A 1960-03-07 1960-03-07
US4883760A 1960-08-11 1960-08-11
US8498061A 1961-01-26 1961-01-26
US8967461A 1961-02-16 1961-02-16
US12363661A 1961-07-13 1961-07-13
US15974661A 1961-12-15 1961-12-15
US217521A US3235357A (en) 1959-08-14 1962-08-17 Method for the control of undesirable vegetation
US221890A US3235358A (en) 1962-09-06 1962-09-06 Control of undesirable vegetation
US232311A US3235360A (en) 1959-08-14 1962-10-22 Control of undesirable vegetation
US233952A US3235361A (en) 1962-10-29 1962-10-29 Method for the control of undesirable vegetation
US284835A US3254082A (en) 1959-08-14 1963-06-03 Process for preparing substituted uracils

Publications (1)

Publication Number Publication Date
GB1035094A true GB1035094A (en) 1966-07-06

Family

ID=27586164

Family Applications (2)

Application Number Title Priority Date Filing Date
GB619566A Expired GB1035096A (en) 1959-08-14 1962-12-07 Improvements relating to herbicides
GB619366A Expired GB1035094A (en) 1959-08-14 1962-12-07 Improvements relating to herbicides and novel 3-substituted uracils

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB619566A Expired GB1035096A (en) 1959-08-14 1962-12-07 Improvements relating to herbicides

Country Status (2)

Country Link
GB (2) GB1035096A (en)
MY (2) MY6900391A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK366887A (en) * 1986-07-31 1988-05-13 Hoffmann La Roche pyrimidine
EP0333791A1 (en) * 1987-09-23 1989-09-27 Ciba-Geigy Ag Heterocyclic compounds
WO1991000278A1 (en) * 1989-06-29 1991-01-10 Ciba-Geigy Ag Heterocyclic compounds

Also Published As

Publication number Publication date
MY6900393A (en) 1969-12-31
MY6900391A (en) 1969-12-31
GB1035096A (en) 1966-07-06

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