GB1073882A - Process for the preparation of biologically active 2,4-pentadienoic acid derivatives - Google Patents

Process for the preparation of biologically active 2,4-pentadienoic acid derivatives

Info

Publication number
GB1073882A
GB1073882A GB15930/65A GB1593065A GB1073882A GB 1073882 A GB1073882 A GB 1073882A GB 15930/65 A GB15930/65 A GB 15930/65A GB 1593065 A GB1593065 A GB 1593065A GB 1073882 A GB1073882 A GB 1073882A
Authority
GB
United Kingdom
Prior art keywords
formula
hydroxy
acid
alkyl
pentadienoic acid
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
GB15930/65A
Inventor
John Warcup Cornforth
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB15930/65A priority Critical patent/GB1073882A/en
Priority to BE679383D priority patent/BE679383A/xx
Priority to FR57299A priority patent/FR1475463A/en
Priority to NL6604832A priority patent/NL6604832A/xx
Priority to ES0325387A priority patent/ES325387A1/en
Priority to SE04962/66A priority patent/SE330012B/xx
Priority to CH523566A priority patent/CH476666A/en
Priority to BR178653/66A priority patent/BR6678653D0/en
Priority to DE1593354A priority patent/DE1593354C3/en
Priority to IL25568A priority patent/IL25568A/en
Priority to DK189366AA priority patent/DK114477B/en
Publication of GB1073882A publication Critical patent/GB1073882A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

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

Abstract

The invention comprises compounds of formula <FORM:1073882/C2/1> in which R, R1, R11 and R111 are H or C1- 4 alkyl, as well as a process for preparing the corresponding (1 - hydroxy - 4 - oxocyclohex - 2-enyl) pentadienoic acid (and its salts and esters) by reacting the (cyclohexa-1,3-dienyl)-pentadienoic acid with activated O2 to give the epidioxide (above) which is then rearranged under alkaline conditions. The hydroxy-oxo acid may be esterified, e.g. with CH2N2. In examples, R = R1 = R11 = R111 = Me. The oxidation step is preferably effected in presence of cosin, erythrosin, fluorescein or chlorophyll.ALSO:Growth of wheat is inhibited by application of a compound of formula <FORM:1073882/C1/1> or of the corresponding (1-hydroxy-4-oxocyclohex-2-enyl) pentadienoic acid, preferably as a composition with a carrier and/or surface-active agent. In the formula, R, R1, R11 and R111 are H or C1- 4 alkyl, preferably methyl. The active compound may be applied in aqueous solution buffered with sodium phosphate.ALSO:Plant growth is inhibited by treating grain and seeds with an epidioxide-containing unsaturated carboxylic acid having the formula: <FORM:1073882/A1-A3/1> or the re-arranged oxo-containing unsaturated carboxylic acid preferably dissolved in water or mixed with a carrier and/or surface-active agent. In the formula, R, R1, R11 and R111 are H or C1-4 alkyl, preferably methyl.
GB15930/65A 1965-04-14 1965-04-14 Process for the preparation of biologically active 2,4-pentadienoic acid derivatives Expired GB1073882A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB15930/65A GB1073882A (en) 1965-04-14 1965-04-14 Process for the preparation of biologically active 2,4-pentadienoic acid derivatives
BE679383D BE679383A (en) 1965-04-14 1966-04-12
FR57299A FR1475463A (en) 1965-04-14 1966-04-12 Process for the preparation of unsaturated carboxylic acids from their esters and their salts
NL6604832A NL6604832A (en) 1965-04-14 1966-04-12
ES0325387A ES325387A1 (en) 1965-04-14 1966-04-12 Procedure for preparing insatured carboxylic acids. (Machine-translation by Google Translate, not legally binding)
SE04962/66A SE330012B (en) 1965-04-14 1966-04-12
CH523566A CH476666A (en) 1965-04-14 1966-04-12 Process for the production of unsaturated carboxylic acids
BR178653/66A BR6678653D0 (en) 1965-04-14 1966-04-12 PROCESS FOR THE PREPARATION OF Unsaturated CARBOXYLIC ACIDS OR THEIR ESTERS OR SALTS
DE1593354A DE1593354C3 (en) 1965-04-14 1966-04-12 Process for the preparation of unsaturated carboxylic acids or their salts or esters
IL25568A IL25568A (en) 1965-04-14 1966-04-12 Unsaturated carboxylic acids and esters and salts thereof,their preparation and use as plant growth regulating agents
DK189366AA DK114477B (en) 1965-04-14 1966-04-13 Process for the preparation of 5- (1-hydroxy-4-oxo-2-cyclohexen-1-yl) -2,4-pentadienoic acids or esters or salts thereof.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB15930/65A GB1073882A (en) 1965-04-14 1965-04-14 Process for the preparation of biologically active 2,4-pentadienoic acid derivatives

Publications (1)

Publication Number Publication Date
GB1073882A true GB1073882A (en) 1967-06-28

Family

ID=10068115

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15930/65A Expired GB1073882A (en) 1965-04-14 1965-04-14 Process for the preparation of biologically active 2,4-pentadienoic acid derivatives

Country Status (11)

Country Link
BE (1) BE679383A (en)
BR (1) BR6678653D0 (en)
CH (1) CH476666A (en)
DE (1) DE1593354C3 (en)
DK (1) DK114477B (en)
ES (1) ES325387A1 (en)
FR (1) FR1475463A (en)
GB (1) GB1073882A (en)
IL (1) IL25568A (en)
NL (1) NL6604832A (en)
SE (1) SE330012B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2193091A (en) * 1986-03-27 1988-02-03 Univ Lancaster Pharmaceutical preparations containing plant growth regulators having calcium agonist or antagonist activity
EP0466353B1 (en) * 1990-06-26 1995-08-30 Toray Industries, Inc. Composition for inhibiting flowering of plants and composition for prolonging duration of flowering of plants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2193091A (en) * 1986-03-27 1988-02-03 Univ Lancaster Pharmaceutical preparations containing plant growth regulators having calcium agonist or antagonist activity
GB2193091B (en) * 1986-03-27 1990-10-24 Univ Lancaster Compounds having calcium-regulatory activity
EP0466353B1 (en) * 1990-06-26 1995-08-30 Toray Industries, Inc. Composition for inhibiting flowering of plants and composition for prolonging duration of flowering of plants

Also Published As

Publication number Publication date
DK114477B (en) 1969-07-07
DE1593354C3 (en) 1975-09-25
IL25568A (en) 1969-11-30
DE1593354A1 (en) 1971-02-25
NL6604832A (en) 1966-10-17
SE330012B (en) 1970-11-02
CH476666A (en) 1969-08-15
ES325387A1 (en) 1967-05-01
BR6678653D0 (en) 1973-09-20
DE1593354B2 (en) 1975-02-13
BE679383A (en) 1966-10-12
FR1475463A (en) 1967-03-31

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