GB913937A - Substituted iminopyrrolidines - Google Patents

Substituted iminopyrrolidines

Info

Publication number
GB913937A
GB913937A GB719059A GB719059A GB913937A GB 913937 A GB913937 A GB 913937A GB 719059 A GB719059 A GB 719059A GB 719059 A GB719059 A GB 719059A GB 913937 A GB913937 A GB 913937A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
groups
group
substituents
cycloaliphatic
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
GB719059A
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 GB913937A publication Critical patent/GB913937A/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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • 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
    • C07D209/02—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
    • 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)

Abstract

The invention comprises compounds of the formula <FORM:0913937/IV (b)/1> and acid addition salts thereof, where R and R5 are organic substituents which are connected to the nitrogen atom through a carbon atom which is itself attached to not more than two other carbon atoms, said substituents being (a) hydrocarbon groups free of non-aromatic unsaturation, (b) hydroxy-substituted aliphatic or cycloaliphatic groups, or (c) groups -R8NR6R7 or -R8OR6, where R8 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups or R7 may be hydrogen; R2 is hydrogen or C1-4 alkyl; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic unsaturation, or R3 or R4 may be hydrogen, or one of the pairs R1R2, 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 four additional carbon atoms; acid addition salts thereof; and their preparation by hydrogenating in the presence of a hydrogenation catalyst at up to 250 DEG C. a compound of formula <FORM:0913937/IV (b)/2> Specified catalysts are Raney nickel, Raney cobalt, cobalt with ammonia, nickel with ammonia, cobalt-copper, nickel-cobalt, palladium, platinum and ruthenium; carriers may be employed. Examples prepare (1) 1-dodecyl-2-dodecylimino-3,3,5-trimethylpyrrolidine, (2) 1-butyl - 2 - butylimino-3,3,5-trimethylpyrrolidine, (3) 1 - benzyl - 2 - benzylimino-3,3,5-trimethylpyrrolidine, and (4) 1-(2-hydroxyethyl)-2 - (2 - hydroxyethylimino) - 3,3,5 - trimethylpyrrolidine. Other products and starting materials are listed, and suitable values for the R group and suitable salt-forming acids are given. The products are pesticides (see Group VI). Specification 913,936 is referred to.ALSO:Pesticidal compositions, e.g. fungicides, comprise a diluent and a compound of formula <FORM:0913937/VI/1> or an acid addition salt thereof, where R and R5 are organic substituents connected to the nitrogen by a carbon atom which is itself attached to not more than two other carbon atoms, said substituents being (a) hydrocarbon groups free of non-aromatic unsaturation, (b) hydroxy-substituted saturated aliphatic or cycloaliphatic groups, or (c) groups -R8NR6R7 or -R8OR6, where R8 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups, or R7 may be hydrogen; R2 is hydrogen or C1-4 alkyl; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic unsaturation, or R3 or R4 may be hydrogen, or one of the pairs R1, R2; R2, R3 and R3, R4, or both 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 four additional carbon atoms (see Group IV (b)). The compositions may be powders, solutions, emulsions or dispersions. Many acid addition salts are specified. Specification 913,936 is referred to.
GB719059A 1958-03-03 1959-03-02 Substituted iminopyrrolidines Expired GB913937A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71850858A 1958-03-03 1958-03-03

Publications (1)

Publication Number Publication Date
GB913937A true GB913937A (en) 1962-12-28

Family

ID=24886335

Family Applications (1)

Application Number Title Priority Date Filing Date
GB719059A Expired GB913937A (en) 1958-03-03 1959-03-02 Substituted iminopyrrolidines

Country Status (1)

Country Link
GB (1) GB913937A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3318909A (en) * 1965-04-21 1967-05-09 Dow Chemical Co Derivatives of 2-cyclohexylimino-pyrrolidine
GB2255557A (en) * 1991-05-01 1992-11-11 Dow Chemical Co Fungicidal compounds, fungicidal compositions, their production and use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3318909A (en) * 1965-04-21 1967-05-09 Dow Chemical Co Derivatives of 2-cyclohexylimino-pyrrolidine
GB2255557A (en) * 1991-05-01 1992-11-11 Dow Chemical Co Fungicidal compounds, fungicidal compositions, their production and use

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