GB913933A - Bis-iminopyrrolines - Google Patents
Bis-iminopyrrolinesInfo
- Publication number
- GB913933A GB913933A GB7186/59A GB718659A GB913933A GB 913933 A GB913933 A GB 913933A GB 7186/59 A GB7186/59 A GB 7186/59A GB 718659 A GB718659 A GB 718659A GB 913933 A GB913933 A GB 913933A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- atoms
- attached
- pairs
- hydrogen
- 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
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
- C07D207/30—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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
Abstract
The invention comprises compounds of the formula <FORM:0913933/IV (b)/1> or a tautomer or acid addition salt thereof, where A is a hydrocarbon group free of nonaromatic unsaturation and which (a) is attached to each nitrogen atom through a carbon atom which itself is attached to not more than two other carbon atoms, (b) contains at least four carbon atoms in a chain between the two nitrogen atoms to which it is attached, and (c) may contain one or more secondary or tertiary amino groups, ether oxygen atoms, or thioether sulphur atoms, each hetero atom being separated from the next by at least two carbon atoms; 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 pairs R1R2 and R3R4 may be joined together to form a cyclohexyl or cyclopentyl 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; and their preparation by reaction of two moles of a cyanoketone <FORM:0913933/IV (b)/2> with one mole of a diamine H2NANH2, e.g. at 40-250 DEG C., in an inert organic solvent which forms an azeotrope with water, the water formed in the reaction being removed azeotropically during the reaction. Other tautomeric forms of the compounds of the invention are <FORM:0913933/IV (b)/3> and <FORM:0913933/IV (b)/4> Examples prepare (1) 1,8-bis(2,4,4-trimethyl-2-pyrrolin-5-ylidene)-1,8-diazaoctane, (2) 1,7-bis (2,4,4 - trimethyl - 2 - pyrrolin-5-ylidene)-1,4,7-triazaheptane, and (3) 1-12-bis(4-methyl-2,4-diphenyl - 2 - pyrrolin - 5 - ylidene)-1,12-diazadodecane. Other products and starting materials and suitable R groups are specified. The compounds of the invention are pesticides (see Group VI).ALSO:Pesticidal compositions, e.g. fungicides comprise a diluent and a compound of formula <FORM:0913933/VI/1> or a tautomer (see Group IV (b)) or acid addition salt thereof, where A is a hydrocarbon group free of non-aromatic unsaturation and which (a) is attached to each nitrogen atom through a carbon atom which itself is attached to not more than two other carbon atoms, (b) contains at least four carbon atoms in a chain between the two nitrogen atoms to which it is attached, and (c) may contain one or more secondary or tertiary amino groups, ether oxygen atoms or thioether sulphur atoms, each hetero atom being separated from the next by at least two carbon atoms; 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; 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 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.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US718503A US2975189A (en) | 1958-03-03 | 1958-03-03 | Bis-iminopyrrolines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB913933A true GB913933A (en) | 1962-12-28 |
Family
ID=24886315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7186/59A Expired GB913933A (en) | 1958-03-03 | 1959-03-02 | Bis-iminopyrrolines |
Country Status (3)
Country | Link |
---|---|
US (1) | US2975189A (en) |
GB (1) | GB913933A (en) |
NL (1) | NL236637A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1229078B (en) * | 1961-10-18 | 1966-11-24 | Hibernia Chemie Ges Mit Beschr | Process for the preparation of 3- (aminomethyl) -3, 5, 5-trimethylcyclohexyl derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE669037C (en) * | 1935-12-07 | 1938-12-15 | Martha Tigges | Spring-loaded clamping device on hand saws |
US2417046A (en) * | 1944-03-07 | 1947-03-11 | Sprague Specialties Co | Synthesis of alkylated pyrrole compounds |
BE477023A (en) * | 1946-05-31 | |||
US2580738A (en) * | 1949-12-23 | 1952-01-01 | Rohm & Haas | N-substituted-2, 5-dimethyl-2, 5-dicyanopyrrolidines |
-
0
- NL NL236637D patent/NL236637A/xx unknown
-
1958
- 1958-03-03 US US718503A patent/US2975189A/en not_active Expired - Lifetime
-
1959
- 1959-03-02 GB GB7186/59A patent/GB913933A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2975189A (en) | 1961-03-14 |
NL236637A (en) |
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