GB1062123A - Cyclic amidines and compositions containing them - Google Patents

Cyclic amidines and compositions containing them

Info

Publication number
GB1062123A
GB1062123A GB2106064A GB2106064A GB1062123A GB 1062123 A GB1062123 A GB 1062123A GB 2106064 A GB2106064 A GB 2106064A GB 2106064 A GB2106064 A GB 2106064A GB 1062123 A GB1062123 A GB 1062123A
Authority
GB
United Kingdom
Prior art keywords
alkyl
carbon atoms
total
aminopropyl
cyclohexylene
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
GB2106064A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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 US284024A external-priority patent/US3305329A/en
Priority claimed from US284025A external-priority patent/US3251854A/en
Priority claimed from US348757A external-priority patent/US3278374A/en
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB1062123A publication Critical patent/GB1062123A/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
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/26—Radicals substituted by carbon atoms having three bonds to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A liquid hydrocarbon fuel has dissolved therein at least one cyclic amidine of the general formula <FORM:1062123/C4-C5/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl, or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenyl-substituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylen or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2 - cyclohexylene and 3,6 - methano - 1,2 - cyclohexenylene; R3 represents hydrogen, 2-hydroxyethyl, 2 - amino - ethyl, 2- or 3-hydroxypropyl, 2- or 3-aminopropyl, 2- or 3-(2-aminoethyl) aminopropyl, 2- or 3-(2- or 3-aminopropyl) aminipropyl, 2-(3-aminopropyl) aminoethyl, or 2-(2-aminoethyl) aminoethyl; and D represents 1,2-cyclohexylene or a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms. Specified fuels are gasolines, jet and diesel fuels and furnace oils and a specified additive is tetraethyl lead.ALSO:The invention comprises cyclic amidines of the general formula <FORM:1062123/C2/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino, or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenyl-substituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylene or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2-cyclohexylene and 3,6 - methano - 1,2 - cyclo-hexenylene; R3 represents hydrogen, 2 - hydroxyethyl, 2-aminoethyl, 2- or 3-hydroxy-propyl, 2- or 3-aminopropyl, 2- or 3-(2-amino-ethyl)aminopropyl, 2- or 3-(2- or 3-amino-propyl)aminopropyl, 2-(3-aminopropyl)amino-ethyl, or 2-(2-aminoethyl)aminoethyl; and D represents 1,2-cyclohexylene or a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms and acid addition salts thereof. These amidines may be prepared by reacting at a temperature at which water is split off an amidoacid of the formula <FORM:1062123/C2/2> with an amine of the formula R3NHDNH2 and, if desired, reacting the cyclic amidine so formed with an acid to form the acid addition salt.ALSO:Biocidal compositions comprise a cyclic amidine of the general formula <FORM:1062123/A5-A6/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl, or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino, or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenylsubstituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylene or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2-cyclohexylene and 3,6-methano -1,2-cyclohexenylene; R3 represents hydrogen, 2-hydroxyethyl, 2-aminoethyl, 2- or 3-hydroxypropyl, 2- or 3-aminopropyl, 2- or 3-(2-aminoethyl) aminopropyl, 2- or 3-(2- or 3-aminopropyl) aminopropyl, 2(3 aminopropyl) aminoethyl or 2(2-aminoethyl) aminoethyl; and D represents 1,2-cyclohexylene as a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms, or an acid-addition salt thereof, together with a diluent. The compositions may also contain specified emulsifying agents, wetting agents, spreading agents, dispersing agents and further unspecified pesticides and may be in the form of wettable powders, emulsions, dusts, granular formulations, aerosols or sprays.
GB2106064A 1963-05-29 1964-05-21 Cyclic amidines and compositions containing them Expired GB1062123A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US28398163A 1963-05-29 1963-05-29
US284024A US3305329A (en) 1963-05-29 1963-05-29 Fuel compositions
US284025A US3251854A (en) 1963-05-29 1963-05-29 Cyclic amidines
US348757A US3278374A (en) 1963-05-29 1964-03-02 Cyclic amidines for control of bacterial and fungal diseases in plants

Publications (1)

Publication Number Publication Date
GB1062123A true GB1062123A (en) 1967-03-15

Family

ID=27501367

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2106064A Expired GB1062123A (en) 1963-05-29 1964-05-21 Cyclic amidines and compositions containing them

Country Status (1)

Country Link
GB (1) GB1062123A (en)

Similar Documents

Publication Publication Date Title
AR032599A1 (en) PROCEDURE FOR PREPARING MANNICH ADUCTS WITH POLYISOBUTENPHENOL CONTENT
KR950700358A (en) Crosslinkable surface coatings
ES2007686A6 (en) Borated amine salts of monothiophosphoric acids.
GB814948A (en) Improvements in and relating to plant growth influencing compositions
JPS6019795B2 (en) lubricating oil composition
ES454491A1 (en) Quaternary ammonioalkanecarboxylic acid anilides as plant growth influencing agents
US4071327A (en) Salts of Mannich bases and derivatives thereof
GB1008463A (en) Dipyridylium salts
GB1071478A (en) Dinitroaniline derivatives and herbicidal compositions containing them
ATE12252T1 (en) LIQUID DETERGENT CONTAINING STAIN-INHIBITING ADDITIVES.
US3975295A (en) Liquid amine compositions
US3455980A (en) Pentacoordinate silicon complexes of vicinal aliphatic diols
US3308161A (en) Alkali metal-dimethyl dodecyl amine salts of oxyacids of phosphorous and sulfur
US4240804A (en) Alkyl acrylate adducts of polyamines, ether amines and ether polyamines
GB1062123A (en) Cyclic amidines and compositions containing them
GB1083549A (en) Multipurpose gasoline additive
JO1077B1 (en) Novel Substituted Heterocyclic Phenoxyamines, The Method of Preparation Thereof and The use Thereof As Local Anaesthetics.
KR930700415A (en) Chemical compositions and their use as fuel additives
US5068046A (en) Lubricant composition comprising an octadecylene oxide polyamine reaction product
GB1063079A (en) Hydroxyphenyl alkanoamides and their use in stabilizing organic materials
US3114649A (en) Fatty derivatives of aminoalkyl and hydroxyalkyl heterocyclic amine bases as asphalt additives
GB903032A (en) Tetrahydropyrimidine carburettor detergent
US3047414A (en) Asphalt compositions and wetting and anti-stripping agents for use in connection therewith
GB1480019A (en) Hydroxyaliphatic esters of n-phosphonomethyl glycine and their use as herbicides
GB790604A (en) Polyamides as fuel oil additives