GB968661A - Herbicidal compositions containing 3-substituted uracils - Google Patents

Herbicidal compositions containing 3-substituted uracils

Info

Publication number
GB968661A
GB968661A GB28141/60A GB2814160A GB968661A GB 968661 A GB968661 A GB 968661A GB 28141/60 A GB28141/60 A GB 28141/60A GB 2814160 A GB2814160 A GB 2814160A GB 968661 A GB968661 A GB 968661A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
compounds
substituted
methyl
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
GB28141/60A
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
Priority to GB17419/64A priority Critical patent/GB968665A/en
Priority to GB17418/64A priority patent/GB968664A/en
Publication of GB968661A publication Critical patent/GB968661A/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
    • 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
    • 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
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

3-Substituted uracils of the isomeric formulae: <FORM:0968661/C1/1> or <FORM:0968661/C1/2> where R1 is a covalent organic radical of molecular weight 15-250 which is C1- 10 alkyl, substituted C1- 3 alkyl, phenyl which may be substituted, C7-8 aralkyl, C7- 12 substituted aralkyl, C3-6 alkenyl, propynyl, butynyl, C5-8 cycloalkyl or cycloalkenyl, or cyano; R2 is hydrogen, halogen, C1-4 alkyl, C1-3 alkoxy NO2, C2-4 alkoxymethyl, hydroxymethyl, hydroxyethyl, allyl, thiocyanato, cyano, halogenomethyl or methylthiomethyl; R3 is hydrogen, chlorine, C1-5 alkyl, methoxy or ethoxy; or R2 and R3 together make up a bridge of formula (CH2)n where n is 3, 4 or 5; and X is oxygen or sulphur; with the proviso that if R2 is hydrogen, then either R3 is C1-5 alkyl and R1 is C3-6 alkyl, allyl, propynyl or C5-8 cycloalkyl or cycloalkenyl; or R3 is hydrogen and R1 is C5-8 cycloalkyl or cycloalkenyl; are prepared by heating a urea R1NH.CX.NH2 with an ester R1OCOCHR2.COR3 (where R1 is C1-6 alkyl) in the presence of an acidic compound and under substantially anhydrous conditions to produce a compound R1NHCXNHCR3=CR2COOR1, and heating this under substantially anhydrous conditions in the presence of a strong base to effect ring closure to give a metal salt (the metal being that of the base) of the compound of the above formula; and acidifying to obtain the free uracil. Novel compounds. The following groups of compounds of the above general formula are claimed as novel: (i) those in which R1 is C5-8 cycloalkyl or cycloalkenyl, or a group -CR5R6R7, where R5 is hydrogen or methyl, R6 is methyl or ethyl, and R7 is C1-5 alkyl; R2 is chlorine or bromine and R3 is methyl; (ii) those in which R1 is C5-8 cycloalkyl or cycloalkenyl, R2 is hydrogen and R3 is C1-5 alkyl; (iii) those in which R1 is as defined in (i) above, and R2 and R3 together make up (CH2)n, where n is 3, 4 or 5; and (iv) those in which R1 is phenyl or substituted phenyl or C5-8 cycloalkyl or cycloalkenyl, R2 is halogen or methyl or nitro, and R3 is hydrogen; and metal salts thereof. Other preparative methods, used in examples are the halogenation of compounds with R2=H to give R2 as chlorine or bromine; nitration of compounds with R2=H to give R2 as NO2; reactions of compounds with R2=H with lead thiocyanate and bromine to give R2 as thiocyanato; reaction of R1NH.CX.NH2 with diethyl oxalacetate or a -substituted oxalacetate followed by acidification (giving e.g. 3-cyclo-hexyluracil-6-carboxylic acid and 3-cyclohexyl-5-methyluracil-6-carboxylic acid) and decarboxylation, giving compounds with R1 in the 3-position, H or the a -substituent in the 5-position (R2) and R3 as hydrogen; reaction of a urea or thiourea substituted by R1 with an alkyl 2-cycloalkanone-1-carboxylate, (giving e.g. 2-(3-methylureido)-1-cyclopentene carboxylic acid ethyl ester) followed by reaction with a base and acidification, giving R2 and R3 as tri-, tetra- or pentamethylene; reaction of compounds with R2=H with formaldehyde to give 5-hydroxymethyl compounds or with chloromethyl methyl ether to give 5-chloromethyl compounds, or converting 5-hydroxymethyl to 5-chloromethyl with thionyl chloride; reaction of 5-chloromethyl compounds with alkoxides or methyl-mercaptides to give R2 as alkoxymethyl or methylthiomethyl; reaction of R1NCO with R3C(NH2)=CHCOOC2H5 followed by ring closure with a base and then acidification; formation of alkali metal salts by reacting a uracil compound with an alkali metal methoxide in alcohol; and formation of other metal salts by metathesis. Many examples are given. The uracils of the formula given are herbicides (see Division A5). Specifications 492,742, 677,342, 968,662, 968,663, 968,664 and 968,665 are referred to.ALSO:Herbicidal compositions comprise at least one compound of the isomeric formul <FORM:0968661/A5-A6/1> or <FORM:0968661/A5-A6/2> where R1 is a covalent organic radical of molecular weight 15-250 which is C1-10 alkyl, substituted C1-3 alkyl, phenyl which may be substituted C7-8 aralkyl, C7-12 substituted aralkyl, C3-6 alkenyl, propynyl, butynyl, cyano or C5-8 cycloalkyl or cycloalkenyl; R2 is hydrogen, halogen, C1-4 alkyl, C1-3 alkoxy, NO2, C2-4 alkoxymethyl, hydroxymethyl, hydroxyethyl, allyl, thiocyanato, cyano, halogenomethyl or methylthiomethyl; R3 is hydrogen, chlorine, C1-5 alkyl, methoxy or ethoxy; or R2 and R3 together make up a bridge of formula (CH2)n, where n is 3, 4 or 5; and X is oxygen or sulphur; with the proviso that if R2 is hydrogen, then either R3 is C1-5 alkyl and R1 is C3-16 alkyl, allyl, propynyl or C5-8 cycloalkyl or cycloalkenyl; or R3 is hydrogen and R1 is C5-8 cycloalkyl or cycloalkenyl; or a metal salt of such a compound (see Division C2), associated with (i) a diluent which is at least in part an oil (see below); (ii) a diluent which is at least in part a solid; (iii) a diluent which is a liquid other than an oil (such as water) and a surface active agent; or (iv) a surface active agent. The invention also comprises a method of controlling the growth of weeds at a locus which comprises applying to the locus a herbicidally effective quantity of a compound of the above formula or a metal salt thereof, if desired in the form of a composition as defined. The subject-matter of Specifications 968,663, 968,664, 968,665 and 968662 is disclaimed. An oil is defined as a liquid immiscible with water and soluble in ether, and which boils at not below 125 DEG C. Suitable oils are aliphatic and aromatic hydrocarbons, e.g. hydrocarbons of petroleum origin. Suitable solid diluents are talc, natural clay, pyrophillite, diatomaceous earth, synthetic fine silica, calcium silicate, magnesium and calcium carbonates, calcium phosphates, sulphur, lime, and flours such as those of walnut shell, wheat, redwood, soya-beam and cottonseeds. Binders used for granular or pellet compositions include goulac, dextrin, swollen starch, glue and polyvinyl alcohol. Conventional additives such as gelatin, blood, albumin, rosin and alkyd resins may also be added. Compositions may also contain other herbicides, such as 2,3,6-trichlorobenzoic acid and salts, 2,3,5,6-tetrachlorobenzoic acid and salts, 2-chloro-N,N-diallylacetamide, N,N-dipropylthiolcarbamic acid ethyl ester, 2,2-dichloropropionic acid and salts, methylarsonic acid and salts, borates, chlorates, ammonium sulphamate, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, N-phenyl carbamic acid isopropyl ester, N-(m-chlorophenyl) carbamic acid isopropyl ester, trichloroacetic acid, maleic hydrazide, 1,1-dimethyl - 3 - (3,4 - dichlorophenyl)urea, 1,1-dimethyl - 3 - (p - chlorophenyl)urea, 1,1-dimethyl - 3 - phenylurea, 1 - n - butyl - 1 - methyl - 3 - (3,4 - dichlorophenyl)urea, 1-methoxy - 1 - methyl - 3 - (3,4 - dichlorophenyl) urea, 1 - methoxy - 1 - methyl - 3 - (p - chlorophenyl)urea, 1,1,3 - trimethyl - 3 - (3,4 - dichlorophenyl)urea, 2 - chloro - 4,6 - bis-(ethylamino) - s - triazine, 2 - chloro - 4 - ethylamino - 6 - isopropylamino - s - triazine, 2-chloro - 4,6 - bis - (methoxypropylamino) - s-triazine, 2 - methoxy - 4,6 - bis - (isopropylamino) - s - triazine, 2,4 - bis - (isopropylamino) - 6 - methoxy - s - triazine, dinitro - secbutylphenol, 2,3,6 - trichlorophenylacetic acid, 5,6 - dihydro - (4A, 6A) - dipyrido-(1,2-A, 21,1-C)-pyrazinium dibromide and 2,6-dichlorobenzonitrile. Other materials employed in specific examples include methyl isobutyl ketone, dibutyl ketone, Na2SO4, Na2HPO4 and sodium pentachlorophenate. Specifications 492,742 and 677,342 also are referred to.
GB28141/60A 1959-08-14 1960-08-15 Herbicidal compositions containing 3-substituted uracils Expired GB968661A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB17419/64A GB968665A (en) 1959-08-14 1960-08-15 3-substituted uracils
GB17418/64A GB968664A (en) 1959-08-14 1960-08-15 3-substituted uracils

Applications Claiming Priority (15)

Application Number Priority Date Filing Date Title
US83370459A 1959-08-14 1959-08-14
US83370559A 1959-08-14 1959-08-14
US1295960A 1960-03-07 1960-03-07
US1295760A 1960-03-07 1960-03-07
US1295660A 1960-03-07 1960-03-07
US1296860A 1960-03-07 1960-03-07
US1295860A 1960-03-07 1960-03-07
US1296760A 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
US232311A US3235360A (en) 1959-08-14 1962-10-22 Control of undesirable vegetation
US284835A US3254082A (en) 1959-08-14 1963-06-03 Process for preparing substituted uracils

Publications (1)

Publication Number Publication Date
GB968661A true GB968661A (en) 1964-09-02

Family

ID=27585449

Family Applications (2)

Application Number Title Priority Date Filing Date
GB28141/60A Expired GB968661A (en) 1959-08-14 1960-08-15 Herbicidal compositions containing 3-substituted uracils
GB17417/64A Expired GB968663A (en) 1959-08-14 1960-08-15 3-substituted uracils

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB17417/64A Expired GB968663A (en) 1959-08-14 1960-08-15 3-substituted uracils

Country Status (12)

Country Link
US (2) US3235360A (en)
BE (1) BE594076A (en)
BR (1) BR6571453D0 (en)
CA (1) CA731651A (en)
CH (1) CH482402A (en)
DE (1) DE1240698C2 (en)
DK (1) DK106253A (en)
GB (2) GB968661A (en)
IT (1) IT635567A (en)
MY (4) MY6500116A (en)
NL (1) NL254838A (en)
SE (1) SE305770B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812164A (en) * 1986-09-18 1989-03-14 Hoffmann-La Roche Inc. Herbicidal heterocyclic compounds
US4859229A (en) * 1986-07-31 1989-08-22 Hoffmann-La Roche Inc. 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety
US5017211A (en) * 1987-09-23 1991-05-21 Ciba-Geigy Corporation Heterocyclic compounds
US5183492A (en) * 1989-06-29 1993-02-02 Ciba-Geigy Corporation Herbicidal 3-aryluracils

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL272286A (en) * 1960-12-27
US3330640A (en) * 1964-05-27 1967-07-11 Du Pont Method for the control of undesirable vegetation
US3436207A (en) * 1965-02-23 1969-04-01 Du Pont Control of undesirable vegetation
US3462435A (en) * 1966-11-15 1969-08-19 United States Borax Chem Alkyleneiminoquinazoline-2,4-diones
US3516816A (en) * 1967-05-19 1970-06-23 United States Borax Chem Herbicidal compositions and methods utilizing alkyleneiminourea compounds
US3532699A (en) * 1968-07-12 1970-10-06 Du Pont Herbicidal poly uracils
US3471282A (en) * 1968-07-12 1969-10-07 Du Pont Herbicidal compositions containing poly uracils
US3539333A (en) * 1968-08-21 1970-11-10 Gulf Research Development Co Combating weeds in sugar beets
US3931171A (en) * 1970-02-05 1976-01-06 Bayer Aktiengesellschaft Process for the production of 2,3-dihydro-1,3-oxazinedione-(2,4)-compounds
US3869275A (en) * 1970-12-04 1975-03-04 Schering Ag Herbicidal mixtures
GB1384506A (en) * 1972-03-24 1975-02-19 American Cyanamid Co 2,3,5-substituted-6-trifluoromethyl-1,3-diazin-4-ones
US4111681A (en) * 1976-09-09 1978-09-05 E. I. Du Pont De Nemours And Company Cycloalkanapyrazole-3-carbonitrile herbicides
US4189366A (en) * 1979-01-15 1980-02-19 Eastman Kodak Company Radiation curable compositions containing 5-halo-6-halomethyluracil derivatives as photoinitiators
FR2498894A1 (en) * 1981-02-04 1982-08-06 Lecalvez Robert Herbicidal compsns. contg. lenacil and a urea (deriv.) - esp. for treatment of ornamental shrubs and conifers
GB8906946D0 (en) * 1988-04-22 1989-05-10 Ici Plc Novel compounds
US5149810A (en) * 1988-04-22 1992-09-22 Imperial Chemical Industries Plc Pyrimidine compounds
EP0354179B1 (en) * 1988-07-29 1994-08-17 Ciba-Geigy Ag Thiouracils as stabilizers for polymers containing chlorine
GB8908638D0 (en) * 1989-04-17 1989-06-01 Ici Plc Novel compounds
US5310723A (en) * 1993-08-05 1994-05-10 Fmc Corporation Herbicidal 3-(1-substituted-quinolin-2-on-7-yl)-1-substituted-6-trifluoromethyluracils
US5391541A (en) * 1993-08-11 1995-02-21 Fmc Corporation Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils
US6344460B1 (en) 1999-03-19 2002-02-05 Lonza Inc. Propynyl uracils
US6409988B1 (en) 1999-07-01 2002-06-25 3-Dimensional Pharmaceuticals, Inc. Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands
US6506784B1 (en) 1999-07-01 2003-01-14 3-Dimensional Pharmaceuticals, Inc. Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides
WO2001007413A1 (en) 1999-07-22 2001-02-01 3-Dimensional Pharmaceuticals, Inc. 1-aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides
AU7865000A (en) 1999-10-06 2001-05-10 3-Dimensional Pharmaceuticals, Inc. Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides
EP2052608A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2090166A1 (en) 2008-02-14 2009-08-19 Bayer CropScience AG Liquid herbicidal preparations
DE102008037631A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
CN114656408A (en) * 2022-04-12 2022-06-24 药源药物化学（上海）有限公司 Synthetic process of plant protectant intermediate

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2937175A (en) * 1960-05-17 Preparation of orotic acid
US2444024A (en) * 1948-06-29 Sydney archer
US2567651A (en) * 1951-09-11 J-dialkyl-g-amino-l
US2899435A (en) * 1959-08-11 S-neopentyl s-aixyl barbituric acid
GB693912A (en) * 1949-04-01 1953-07-08 Us Rubber Co Plant growth regulants and phytocides
US2688020A (en) * 1952-01-17 1954-08-31 American Cyanamid Co Preparation of dihydrouracils
US2820035A (en) * 1953-10-07 1958-01-14 Boehringer Sohn Ingelheim Barbituric acid derivatives
BE553585A (en) * 1955-12-21
NL99656C (en) * 1956-04-04
US3078154A (en) * 1956-11-07 1963-02-19 Geigy Ag J R Method for inhibiting the growth of plants
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
US3086854A (en) * 1959-02-05 1963-04-23 Du Pont Method for the control of plant growth

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859229A (en) * 1986-07-31 1989-08-22 Hoffmann-La Roche Inc. 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety
US4812164A (en) * 1986-09-18 1989-03-14 Hoffmann-La Roche Inc. Herbicidal heterocyclic compounds
US5017211A (en) * 1987-09-23 1991-05-21 Ciba-Geigy Corporation Heterocyclic compounds
US5183492A (en) * 1989-06-29 1993-02-02 Ciba-Geigy Corporation Herbicidal 3-aryluracils

Also Published As

Publication number Publication date
IT635567A (en) 1900-01-01
BE594076A (en) 1900-01-01
NL254838A (en) 1900-01-01
MY6500116A (en) 1965-12-31
US3235360A (en) 1966-02-15
GB968663A (en) 1964-09-02
CH482402A (en) 1969-12-15
MY6500115A (en) 1965-12-31
DE1240698B (en) 1973-01-04
MY6500103A (en) 1965-12-31
US3254082A (en) 1966-05-31
CA731651A (en) 1966-04-05
DK106253A (en) 1900-01-01
SE305770B (en) 1968-11-04
BR6571453D0 (en) 1973-05-10
MY6500102A (en) 1965-12-31
DE1240698C2 (en) 1973-01-04

Similar Documents

Publication Publication Date Title
GB968661A (en) Herbicidal compositions containing 3-substituted uracils
IE791064L (en) Pyrimidine and triazine derivatives
DK179681A (en) METHOD OF PREPARING ACYLCYANIDES
CA1180336A (en) Herbicidal pyridine derivatives
CS204033B2 (en) Herbicide means
US3360523A (en) 3, 5, 6-substituted hydrouracils
US3322526A (en) Herbicidal composition and method
US2788360A (en) Preparation of dicyano halo-ethane cyclic compounds
KR920006782B1 (en) Pyrimidine derivatives
US3646136A (en) 2-ureido-benzamides their production and use
US3634509A (en) 2 6-dinitroanilinoacetamides
GB1108838A (en) O-methyl-n-isopropylamido-o-(2-nitrophenyl)-thionophosphoric acid ester
US4012519A (en) Fungicidal 3-(N-acyl-N-arylamino) lactones and lactams
US4353830A (en) Process for the preparation of substituted amidines
US3399988A (en) Method of controlling the growth of weeds
CA1149392A (en) Heterocyclic phenoxyalkanoic acid derivatives
US2569425A (en) Methoxy-ethyl esters of imido acids
US3122543A (en) N-(alkoxyalkyl)-4, 7-diamino-2-aryl-6-pteridinecarboxamides
NZ226419A (en) 1,5-diphenyl-1,2,4-triazole-3-carboxylic acid derivatives and compositions affording protection from the phytotoxic action of herbicides
US3629261A (en) Chloropyrimidine derivatives
CA2006075A1 (en) Process for the preparation of pyrimidine derivatives
US3812168A (en) 2-(n&#39;-methoxy-n&#39;-methyl-ureido)-benzamide
US4841089A (en) Process for the preparation of 4-mercaptobenzonitriles, and 4-mercaptobenzonitriles
US4716229A (en) New pyrimidines and a process for the preparation of pyrimidines
EP0198054A1 (en) Process for preparing substituted amino herbicides