GB1035091A - Improvements relating to herbicides - Google Patents

Improvements relating to herbicides

Info

Publication number
GB1035091A
GB1035091A GB4634262A GB4634262A GB1035091A GB 1035091 A GB1035091 A GB 1035091A GB 4634262 A GB4634262 A GB 4634262A GB 4634262 A GB4634262 A GB 4634262A GB 1035091 A GB1035091 A GB 1035091A
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
GB4634262A
Inventor
Harvey Monroe Loux
Edward John Soboczenski
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 GB4634262A priority Critical patent/GB1035091A/en
Publication of GB1035091A publication Critical patent/GB1035091A/en
Priority to MY6900398A priority patent/MY6900398A/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
    • 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
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Compounds of the formula <FORM:1035091/C2/1> or the corresponding isomeric formula <FORM:1035091/C2/2> wherein X represents an oxygen or sulphur atom and R1, R2 and R3 are 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 or a cyano radical; 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 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 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; (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 or a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 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 or a cyano radical; 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, 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 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; 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, and R3 represents a hydrogen atom; and metal salts of compounds as defined above, are prepared by methods known for the preparation of uracils, e.g. those disclosed in Specification 968,661. Compounds of the above formulae in which X is oxygen, and (1) R1 is C3- 10 cycloalkyl which may be substituted, or C4- 10 cycloalkenyl which may be substituted, and R2 and R3 together represent (CH2)n where n is 3, 4 or 5, or (2) R1 is C3- 12 cycloalkyl which may be substituted, or C5- 12 cycloalkenyl which may be substituted, R2 is halogen, methyl, hydroxymethyl, methoxymethyl or nitro, and R3 is hydrogen, are claimed as novel. The uracils as defined above are herbicides (see Division A5). Intermediates.-Malononitrile is reacted with (i) norbornylurea and triethyl orthoacetate and (ii) fenchylurea and triethyl orthoformate to give respectively [1-(3-norbornylureido)ethylidene] malonitrile and [(3-fenchylureido)methylene] malononitrile, which with methanolic NaOMe followed by acetic acid produce 3-norbornyl-6-methyl-5-cyanocytosine and 3-fenchyl-5-cyanocytosine respectively. sec-Butylurea and 2-acetyl-4-butylbutyrolactone are reacted to produce 2-(2-hydroxyhexyl)-3-(3-sec-butylureido) -crotonic acid lactone.ALSO:Compounds of the formula <FORM:1035091/A5-A6/1> or the corresponding isomeric formula: <FORM:1035091/A5-A6/2> wherein X represents an oxygen or sulphur atom and R1, R2 and R3 are 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 or a cyano radical; 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; R3 represents a 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; (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 or a substituted p cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 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 or a cyano radical; 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, 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 cy
GB4634262A 1962-12-07 1962-12-07 Improvements relating to herbicides Expired GB1035091A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB4634262A GB1035091A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides
MY6900398A MY6900398A (en) 1962-12-07 1969-12-31 Improvements relating to herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4634262A GB1035091A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides

Publications (1)

Publication Number Publication Date
GB1035091A true GB1035091A (en) 1966-07-06

Family

ID=10440858

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4634262A Expired GB1035091A (en) 1962-12-07 1962-12-07 Improvements relating to herbicides

Country Status (2)

Country Link
GB (1) GB1035091A (en)
MY (1) MY6900398A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0881223A1 (en) * 1996-02-09 1998-12-02 Kumiai Chemical Industry Co., Ltd. Benzofuran-7-yluracil derivatives and herbicides

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US5104878A (en) * 1989-04-17 1992-04-14 Imperial Chemical Industries Plc 1-phenyl-6-one-pyrimidine derivatives
EP0881223A1 (en) * 1996-02-09 1998-12-02 Kumiai Chemical Industry Co., Ltd. Benzofuran-7-yluracil derivatives and herbicides
EP0881223A4 (en) * 1996-02-09 1999-04-14 Kumiai Chemical Industry Co Benzofuran-7-yluracil derivatives and herbicides
US6130187A (en) * 1996-02-09 2000-10-10 Kumiai Chemical Industry Co., Ltd. Benzofuran-7-yl uracil derivatives and herbicides

Also Published As

Publication number Publication date
MY6900398A (en) 1969-12-31

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