GB1035097A - Improvements relating to herbicides - Google Patents

Improvements relating to herbicides

Info

Publication number
GB1035097A
GB1035097A GB619666A GB619666A GB1035097A GB 1035097 A GB1035097 A GB 1035097A GB 619666 A GB619666 A GB 619666A GB 619666 A GB619666 A GB 619666A GB 1035097 A GB1035097 A GB 1035097A
Authority
GB
United Kingdom
Prior art keywords
radical
carbon atoms
radical containing
substituted
alkyl
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
GB619666A
Inventor
Edward John Soboczenski
Raymond Wilson Luckenbaugh
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 GB619666A priority Critical patent/GB1035097A/en
Publication of GB1035097A publication Critical patent/GB1035097A/en
Priority to MY6900388A priority patent/MY6900388A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines

Abstract

Novel compounds of the general formula <FORM:1035097/C2/1> or the corresponding isomeric formula <FORM:1035097/C2/2> wherein 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 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 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms or a cyano radical; 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; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent radical which forms, together with the carbon atoms to which R2 and R3 are attached, a 5-, 6- or 7-membered ring; R4 represents a covalent radical of molecular weight from 15 to 250 which is an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms (which may be substituted), a cycloalkylalkyl radical containing 4 to 13 carbon atoms (which may be substituted), a phenyl radical, a substituted phenyl radical, a phenylalkyl radical, a substituted phenylalkyl radical, a dialkylamino radical containing 2 to 10 carbon atoms, an alkoxy radical containing 1 to 10 carbon atoms, a carbamyl radical, a substituted carbamyl radical, a thiocarbamyl radical, a substituted thiocarbamyl radical, a glycosyl radical, a cyano radical, an acyl radical, a carboxyethyl radical, a dialkoxyphosphoryl radical containing 2 to 6 carbon atoms, an alkylthio radical containing 1 to 12 carbon atoms, a bromoalkylthio radical containing 1 to 12 carbon atoms, a chloroalkylthio radical containing 1 to 12 carbon atoms, a benzylthio radical, a phenylthio radical, a halophenylthio radical, a mononitrophenylthio radical, a p-tert.-butyphenylthio radical, a dinitrophenylthio radical or a tolythio radical; and X represents an oxygen or sulphur atom, are prepared by methods known for related compounds, e.g. those disclosed in Specification 968,666. These compounds are herbicides (see Division A5). Compounds of the above formulae in which X is oxygen, R1 is as defined, R2 is halogen, R3 is methyl, and R4 is CCl3S- or RCO-, where R is hydrogen, C1- 4 alkyl, a mono- or polychloroalkyl radical of 1-4 C, phenyl, mono-, di- or trichlorophenyl, benzyl, mono-, di- or trichlorobenzyl, phenoxymethyl or mono-, di- or trichlorophenoxymethyl, are claimed as novel. b - Isopropylamino - N - isopropylcrotonamide is prepared from N-isopropylacetoacetamide and isopropylamine.ALSO:Compounds of the general formula <FORM:1035097/A5-A6/1> or the corresponding isomeric formula <FORM:1035097/A5-A6/2> wherein 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 7 to 15 carbon atoms, an alkenyl 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 or a cyano radical; 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 mercapto-methyl 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; R3 represents a hydrogen, chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms; or R2 and R3 together represent a divalent radical which forms, together with the carbon atoms to which R2 and R3 are attached, a 5-, 6- or 7-membered ring; R4 represents a covalent radical of molecular weight from 15 to 250 which is an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms (which may be substituted), a cycloalkylalkyl radical containing 4 to 13 carbon atoms (which may be substituted), a phenyl radical, a substituted phenyl radical, a phenylalkyl radical, a substituted phenylalkyl radical, a dialkylamino radical containing 2 to 10 carbon atoms, an alkoxy radical containing 1 to 10 carbon atoms, a carbamyl radical, a substituted carbamyl radical, a thiocarbamyl radical, a substituted thiocarbamyl radical, a glycosyl radical, a cyano radical, an acyl radical, a carboxyethyl radical, a dialkoxyphosphoryl radical containing 2 to 6 carbon atoms, an alkylthio radical containing 1 to 12 carbon atoms, a bromoalkylthio radical containing 1 to 12 carbon atoms, a benzylthio radical, a phenylthio radical, a halophenylthio radical, a mononitro-phenylthio radical, a p-tert-butylphenylthio radical, a dinitrophenylthio radical or a tolylthio radical; and X represents an oxygen or sulphur atom, are used to control the growth of weeds, e.g. in a composition containing additionally (i) a diluent which is at least in part an oil (defined as a liquid immiscible with water and soluble in ether, and boiling at not below 125 DEG C.), with or without a surface-active agent; (ii) a diluent which is at least in part a solid, with or without a surface-active agent; (iii) a surface-active agent and a diluent which is a liquid other than an oil, e.g. water; or (iv) a surface-active agent. The compositions may be in the form of solutions, dispersions, powders or dusts, granules or pellets, and may contain adhesives, corrosion inhibitors, antifoam agents, dyes, pigments, anticaking agents, hard water stabilizers and other herbicides, e.g. those of Specifications 1,035,091, 1,035,092, 1,035,093, 1,035,094, 1,035,095, 1,035,096 and 1,035,098 or substituted ureas, substituted trianzines, phenols, chloro-carboxylic acids and their derivatives, substituted carbamic acid derivatives, maleic hydrazide, inorganic salts, mixed inorganic-organic salts, or other specified herbicides.
GB619666A 1962-12-07 1962-12-07 Improvements relating to herbicides Expired GB1035097A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB619666A GB1035097A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides
MY6900388A MY6900388A (en) 1962-12-07 1969-12-31 Improvements relating to herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB619666A GB1035097A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides

Publications (1)

Publication Number Publication Date
GB1035097A true GB1035097A (en) 1966-07-06

Family

ID=9810164

Family Applications (1)

Application Number Title Priority Date Filing Date
GB619666A Expired GB1035097A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides

Country Status (2)

Country Link
GB (1) GB1035097A (en)
MY (1) MY6900388A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2172345A1 (en) * 1972-02-18 1973-09-28 Bayer Ag
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
US4990512A (en) * 1988-08-04 1991-02-05 Imperial Chemical Industries Plc Pyridyl-pyrimidones
US5017211A (en) * 1987-09-23 1991-05-21 Ciba-Geigy Corporation Heterocyclic compounds
US5077297A (en) * 1988-04-22 1991-12-31 Imperial Chemical Industries Plc Novel compounds
US5104878A (en) * 1989-04-17 1992-04-14 Imperial Chemical Industries Plc 1-phenyl-6-one-pyrimidine derivatives
US5149810A (en) * 1988-04-22 1992-09-22 Imperial Chemical Industries Plc Pyrimidine compounds
US5183492A (en) * 1989-06-29 1993-02-02 Ciba-Geigy Corporation Herbicidal 3-aryluracils

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2172345A1 (en) * 1972-02-18 1973-09-28 Bayer Ag
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
US5077297A (en) * 1988-04-22 1991-12-31 Imperial Chemical Industries Plc Novel compounds
US5149810A (en) * 1988-04-22 1992-09-22 Imperial Chemical Industries Plc Pyrimidine compounds
US4990512A (en) * 1988-08-04 1991-02-05 Imperial Chemical Industries Plc Pyridyl-pyrimidones
US5104878A (en) * 1989-04-17 1992-04-14 Imperial Chemical Industries Plc 1-phenyl-6-one-pyrimidine derivatives
US5183492A (en) * 1989-06-29 1993-02-02 Ciba-Geigy Corporation Herbicidal 3-aryluracils

Also Published As

Publication number Publication date
MY6900388A (en) 1969-12-31

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