GB1115786A - Uracil compounds and their use as herbicides - Google Patents

Uracil compounds and their use as herbicides

Info

Publication number
GB1115786A
GB1115786A GB51052/65A GB5105265A GB1115786A GB 1115786 A GB1115786 A GB 1115786A GB 51052/65 A GB51052/65 A GB 51052/65A GB 5105265 A GB5105265 A GB 5105265A GB 1115786 A GB1115786 A GB 1115786A
Authority
GB
United Kingdom
Prior art keywords
uracils
salts
group
substituted
hydrogen
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
GB51052/65A
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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1115786A publication Critical patent/GB1115786A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises uracils of the formula <FORM:1115786/C2/1> where AN- is a cycloimino group containing 2-14 carbon atoms and at most 3 hetero atoms, X is oxygen or sulphur, R1 is hydrogen, chlorine, fluorine, bromine, iodine or a nitro, C1- 4 alkyl, C1- 4 alkoxy, hydroxymethyl or C2- 5 alkoxymethyl group, R2 is a C1- 3 alkyl group and R3 is hydrogen or a C1- 3 alkyl group or R1 and R2 together form a radical -(CH\2)n-, where n is 3, 4 or 5, and the salts and complexes of such uracils. The uracils are prepared by condensing an appropriately substituted urea with an a -substituted-b -keto ester, treating the resulting ureido compound with a base, followed by acidification to separate the uracil. If a b -keto-ester unsubstituted in the a -position is used, the resulting uracil can be converted to the required 5-substituted compound using conventional chlorination, bromination, iodination, nitration, formylation and alkylation processes. The 4-thiouracils can be made by treating the corresponding di-oxo compounds with phosphorus penta-sulphide. The salts and complexes may be those formed with inorganic or organic bases or acids and phenols. A large number of compounds are specified including those in which the cycloimino group is a hexahydro-1-azepinyl, morpholino, piperidino, 1-pyrrolidinyl, 10-phenothiazinyl, dihydro-1,3,5-dithiazin-5-yl, 1-aziridinyl, 1,2,3,6 -tetrahydro - 1 - pyridyl, 1 - piperazinyl, 9 - carbosolyl, 4 - pyrazolin - 1 - yl, tetrahydro - 1,4 - thiazin - 4 - yl, dihydro - 1,3,5dioxazin - 5 - yl, 1,2,3,4 - tetrahydro - 2 - isoquinolinyl, 3 - azabicyclo(3.2.2)nonan - 3 - yl, 1 - benzimidazolyl and 4 - pipecolin - 1 - yl group. The uracils are used as herbicides (see Division A5).ALSO:Herbicidal compositions comprise uracils of the formula <FORM:1115786/A5-A6/1> where A \s6 N is a cycloimino group containing 2-14 carbon atoms and at most 3 - hetero atoms, X is oxygen or sulphur, R1 is hydrogen, chlorine, bromine, fluorine or iodine or a nitro, C1-4 alkyl, C1-4 alkoxy, hydroxymethyl or C2-5 alkoxymethyl group, R2 is a C1-3 alkyl group and R3 is hydrogen or a C1-3 alkyl group, or R1 and R2 together represent - (CH2)n - where n is 3,4 or 5 and salts and complexes of such uracils. In addition to the usual diluents and additives the compositions may include other herbicidal compounds. A large number of known herbicides are specified and include substituted ureas, substituted triazines, phenols, carboxylic acids and salts, esters, amides, hydrasides and nitriles thereof, thiolcarbamates, inorganic salts, mixed inorganic/organic salts, amines, quarternary ammonium compounds, other substituted uracils and chlorinated ketones. Examples 262-273 relate to the preparation and application of the uracil composi. tions.
GB51052/65A 1964-12-07 1965-12-01 Uracil compounds and their use as herbicides Expired GB1115786A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41662364A 1964-12-07 1964-12-07
US690077A US3397050A (en) 1964-12-07 1967-12-13 Herbicidal method

Publications (1)

Publication Number Publication Date
GB1115786A true GB1115786A (en) 1968-05-29

Family

ID=27023425

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51052/65A Expired GB1115786A (en) 1964-12-07 1965-12-01 Uracil compounds and their use as herbicides

Country Status (5)

Country Link
US (1) US3397050A (en)
CH (1) CH480013A (en)
DE (1) DE1567038A1 (en)
FR (1) FR1461796A (en)
GB (1) GB1115786A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3497344A (en) * 1966-11-15 1970-02-24 United States Borax Chem Herbicidal compositions and methods utilizing uramidobenzoate compounds
US6376426B1 (en) 1999-04-23 2002-04-23 Basf Aktiengesellschaft Herbicidal 3-(heterocycl-1-yl)-uracils

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2969364A (en) * 1957-12-26 1961-01-24 Upjohn Co Derivatives of 5-amino uracil
US3002975A (en) * 1958-08-25 1961-10-03 Diamond Alkali Co Process for the preparation of 1,3-dihalo-uracils
US3235357A (en) * 1959-08-14 1966-02-15 Du Pont Method for the control of undesirable vegetation

Also Published As

Publication number Publication date
CH480013A (en) 1969-10-31
FR1461796A (en) 1966-12-09
US3397050A (en) 1968-08-13
DE1567038A1 (en) 1970-06-25

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