GB913931A - Iminopyrrolines - Google Patents

Iminopyrrolines

Info

Publication number
GB913931A
GB913931A GB710559A GB710559A GB913931A GB 913931 A GB913931 A GB 913931A GB 710559 A GB710559 A GB 710559A GB 710559 A GB710559 A GB 710559A GB 913931 A GB913931 A GB 913931A
Authority
GB
United Kingdom
Prior art keywords
group
hydrogen
pyrroline
trimethyl
saturated aliphatic
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
GB710559A
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
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB913931A publication Critical patent/GB913931A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0913931/IV (b)/1> or a tautomer thereof of formula <FORM:0913931/IV (b)/2> or <FORM:0913931/IV (b)/3> where R is hydrogen or an organic substituent connected to the nitrogen through a carbon atom which in turn is attached to not more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of acetylenic unsaturation, (b) a hydroxy-substituted saturated aliphatic or cycloaliphatic group, or (c) a group -R5NR6R7 or -R5OR6, where R5 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency also carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups and R7 can be hydrogen; R2 is hydrogen or C1-4 alkyl group; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic substitution, with the provisos that R3 and R4 may be hydrogen, and that one of the pairs R1R2, R1R3, R2R3 and R3R4, or both the pairs R1R2 and R3R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than 4 additional carbon atoms. These compounds are prepared by the reaction between one mole of a cyanoketone <FORM:0913931/IV (b)/4> and one mole of ammonia or an amine RNH2, preferably at 40-250 DEG C. in the presence of an inert organic solvent which forms an azeotrope with water, the water formed in the reaction being removed azeotropically during the reaction. Intermediates of the formula <FORM:0913931/IV (b)/5> are generally formed, and are converted to the desired products by heating. Examples prepare (1) 2,4,4-trimethyl-5-laurylimino-2-pyrroline, (2) 2-methyl-5-laurylimino-2-pyrroline, (3) 2,4,4-trimethyl-5-octadecylimino-2-pyrroline, (4) 2,4,4, - trimethyl-5-cyclohexylimino-2-pyrroline, (5) and (10) 2,4, 4-trimethyl-5-methylimino-2-pyrroline, (6) 2,4,4-trimethyl-5-butylimino-2-pyrroline, (7) and (9) 2,4,4-trimethyl-5-benzylimino-2-pyrroline, and (8) 2,4,4 - trimethyl - 5 - phenylimino-2-pyrroline. Other products are specified, suitable cyanoketones and amines are listed, and suitable values for the R groups are given. The compounds of the invention are pesticides (see Group VI). Specifications 913,932, 913,933, 913,934, 913,935, 913,936, 913,937 and 913,938 are referred to.ALSO:Pesticidal compositions comprise a diluent and one or more compounds of formula <FORM:0913931/VI/1> or a tautomer thereof (see Group IV (b)), where R is hydrogen or an organic substituent connected to the nitrogen through a carbon atom which in turn is attached to not more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of acetylenc unsaturation, (b) a hydroxy-substituted saturated aliphatic or cycloaliphatic group, or (c) a group -R5NR6R7 or -R5OR6, where R5 is a saturated aliphatic or cycloaliphatic group, and R6 and R7 are saturated aliphatic or cycloaliphatic groups or R7 can be hydrogen; R2 is hydrogen or C1-4 alkyl; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic unsaturation, or R3 and R4 may represent hydrogen, or one of the pairs R1, R2; R1, R3; R2, R3; and R3, R4, or both the pairs R1, R2 and R3, R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than 4 additional carbon atoms (see Group IV (b)). The compositions may be powders, solutions, emulsions or dispersions. Specifications 913,932, 913,933, 913,934, 913,935, 913,936, 913,937 and 913,938 are referred to.
GB710559A 1958-03-03 1959-03-02 Iminopyrrolines Expired GB913931A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71850158A 1958-03-03 1958-03-03

Publications (1)

Publication Number Publication Date
GB913931A true GB913931A (en) 1962-12-28

Family

ID=24886305

Family Applications (1)

Application Number Title Priority Date Filing Date
GB710559A Expired GB913931A (en) 1958-03-03 1959-03-02 Iminopyrrolines

Country Status (3)

Country Link
DE (1) DE1175238B (en)
GB (1) GB913931A (en)
NL (1) NL236636A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984563A (en) * 1973-09-10 1976-10-05 Gruppo Lepetit S.P.A. Antiinflammatory 2-imino-indolines and their pharmaceutical compositions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984563A (en) * 1973-09-10 1976-10-05 Gruppo Lepetit S.P.A. Antiinflammatory 2-imino-indolines and their pharmaceutical compositions

Also Published As

Publication number Publication date
DE1175238B (en) 1964-08-06
NL236636A (en)

Similar Documents

Publication Publication Date Title
GB862250A (en) Improvements in or relating to thiolcarbamates
GB1164824A (en) Nitro-Paraphenylene-Diamines and their use as Hair Dyes
GB1288678A (en)
GB999585A (en) Bipyridylium compounds and herbicidal compositions containing them
GB913931A (en) Iminopyrrolines
SE322775B (en)
GB1080807A (en) Heterocyclic amino-isobutyl compounds
GB975845A (en) Amides of o,o-bis-fluoroalkyldithiophosphoryl-acetic acids
GB913933A (en) Bis-iminopyrrolines
GB1318139A (en) Dinitro-1,3-phenylenediamine compounds and herbicidal compositions containing them
GB1071507A (en) Substituted ureas and herbicidal compositions containing them
ES425533A1 (en) Dichlorothiazolylureas processes for their preparation and their use as herbicides
GB913932A (en) Iminopyrrolidines
GB913936A (en) Substituted iminopyrrolines
GB796484A (en) O-aryl o-methyl phosphoroamidothioates
GB880297A (en) Phosphoric and thionophosphoric acid ester amides and diamides
GB890540A (en) Urea derivatives
GB1221389A (en) 2,4-dicyano-6-nitrobenzene derivatives
GB1436567A (en) Use of coumarilic acid amides as herbicides
GB986547A (en) Herbicidal compositions
GB898415A (en) Novel phosphoric acid alkyl alkinyl ester monoamides, and process for the production thereof
ES375323A1 (en) New n-alkoxyalkylene-alkyl ureas and compositions containing them
GB913937A (en) Substituted iminopyrrolidines
GB1079224A (en) Process for the production of pyridazinone derivatives
GB898068A (en) Amino compounds