GB760686A - Oxygen-bridged hydrogenated derivatives of phthalamic acid - Google Patents

Oxygen-bridged hydrogenated derivatives of phthalamic acid

Info

Publication number
GB760686A
GB760686A GB818853A GB818853A GB760686A GB 760686 A GB760686 A GB 760686A GB 818853 A GB818853 A GB 818853A GB 818853 A GB818853 A GB 818853A GB 760686 A GB760686 A GB 760686A
Authority
GB
United Kingdom
Prior art keywords
exo
cis
specified
salts
mono
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
GB818853A
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.)
Pennsylvania Salt Manufacturing Co
Original Assignee
Pennsylvania Salt Manufacturing 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 to US254189A priority Critical patent/US2637644A/en
Application filed by Pennsylvania Salt Manufacturing Co filed Critical Pennsylvania Salt Manufacturing Co
Priority to GB818853A priority patent/GB760686A/en
Publication of GB760686A publication Critical patent/GB760686A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08Bridged systems

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

Abstract

The invention comprises acids of exo-cis configuration conforming to the formula <FORM:0760686/IV(b)/1> wherein R1 and R2 each represents hydrogen or an alkyl, hydroxyalkyl or cycloalkyl radical, or together represent a polymethylene or oxapolymethylene radical; and the water-soluble salts thereof. Lists of suitable R1 and R2 substituents are specified; these have preferably 1 to 12 carbon atoms. Suitable polymethylene and oxapolymethylene radicals are tetramethylene, pentamethylene, hexamethylene, and 3-oxapentamethylene radicals. Watersoluble salts are those of alkali metals, alkaline earth metals, aluminium and heavy metals; ammonium, mono-, di-, and trialkylammonium, mono-, di-, and trialkanolammonium, mixed alkylalkanolammonium, and mono-, and dicycloalkylammonium salts (lists of each being specified); and salts of heterocyclic amines such as morpholine, piperidine, pyrrolidine, and hexamethyleneimine. The compounds are prepared by reacting exo-cis-3,6-endoxohexahydrophthalic anhydride with ammonia or a primary or secondary amine in an aqueous or nonaqueous medium such as hexane, kerosene, benzene, toluene or xylene. A list of suitable amine reactants is specified. Salts are obtained by employing excess of amine reactant or by subsequent neutralization of the free acid. A list of suitable acids is specified. The examples describe the preparation of 3,6-endoxohexahydrophthalamic acid, N,N-diisopropyl- and N-butyl-3,6-endoxohexahydrophthalamic acid, butylammonium N-butyl-, dibutylammonium N,N-dibutyl-, diethylammonium N,N-diethyl-, diisopropylammonium N,N-diisopropyl-, and ammonium 3,6-endoxohexahydrophthalamate, all of exo-cis configuration.ALSO:Herbicides, defoliants and like plant response agents comprise acids of exo-cis configuration conforming to the formula: <FORM:0760686/I/1> wherein R1 and R2 each represents hydrogen or an alkyl, hydroxyalkyl or cycloalkyl radical, or together represent a polymethylene or oxapolymethylene radical; or the water-soluble salts thereof, together with at least one additional ingredient compatible therewith. Lists of suitable R1 and R2 substituents are specified; these have preferably 1 to 12 carbon atoms. Suitable polymethylene and oxapolymethylene radicals are tetramethylene, pentamethylene, hexamethylene, and 3-oxapentamethylene radicals. Specified water-soluble salts are those of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury and copper; ammonium, mono-, di-, and tri-alkylammonium, mono-, di-, and trialkanolammonium, mixed alkylalkanolammonium and mono-, and dicycloalkylammonium salts (lists of each being specified); and salts of heterocyclic amines such as morpholine, piperidine, pyrrolidine, and hexamethyleneimine. The additional ingredient may be (1) a liquid carrier in which the active ingredient is dissolved or dispersed such as water, oils of petroleum, animal, vegetable, or synthetic origin (e.g. kerosene, fuel, lubricating, soybean, linseed, castor, sperm and cod liver oils), (2) a wetting or dispersing agent such as a fatty alcohol sulphate, an aliphatic, aromatic or alkaryl sulphonate, an alkyl polyglycolether or the anologous thioether (examples are specified), (3) a solid carrier such as a clay (e.g. Fuller's earth, pyrophyllite, talc, bentonite, kieselguhr and diatomaceous earth), sulphur, volcanic ash, calcium carbonate, lime, by-product lignin, lignocellulose, flour (e.g. from wood, walnut shell, wheat, soybean, potato and cotton seed) (4) a humectant such as glycerine, diethylene glycol, ethylene glycol, polyethylene glycols, water-soluble sugars and sugar-containing mixtures (e.g. glucose, fructose, galactose, mannose, arabinose, xylose, sucrose, maltose, lactose, raffinose and trehalose), dextrins (e.g. white dextrin, canary dextrin and British gum), honey, molasses, maple syrup, maple sugar, corn syrup and other starch syrups, (5) any combination of (1), (2), (3) and (4). The resulting compositions may also include fungicides, insecticides, bactericides and other types of plant response agents. Preferred active ingredients are dimethylammonium exo-cis-N, N-dimethyl-, diethylammonium exo-cis-N, N-diethyl, and dibutylammonium exo-cis-N, N-dibutyl-3, 6-endoxohexahydrophthalamate, exo-cis-N, N-diethyl-, and exo-cis-N, N-diisopropyl-3, 6-endoxohexahydrophalanic acid. The examples describe (1) a dust comprising exo-cis-N-butyl-3, 6-endoxohexahydrophthalamic acid, talc and sodium dodecylbenzene sulphonate (2) a composition suitable for application as an aqueous dispersion comprising dimethyl-ammonium exo-cis-N, N-dimethyl-, or butyl-ammonium exo-cis-N-butyl-3, 6- endoxohexahydrophthalamate, Fuller's earth and lignin sulphonate (3) an oil-in-water emulsion prepared by stirring an aqueous solution of exo-cis-N, N-diisopropyl-3, 6-endoxohexahydrophthalamic acid and sorbitol oleate ethylene oxide with diesel oil.ALSO:Herbicides, defoliants and like plant response agents comprise acids of exo-cis configuration conforming to the formula <FORM:0760686/VI/1> wherein R1 and R2 each represents hydrogen or an alkyl, hydroxy-alkyl or cycloalkyl radical, or together represent a polymethylene or oxapolymethylene radical; or the water-soluble salts thereof, together with at least one additional ingredient compatible therewith. Lists of suitable R1 and R2 substituents are specified; these have preferably 1 to 12 carbon atoms. Suitable polymethylene and oxapolymethylene radicals are tetramethylene, pentamethylene, hexamethylene, and 3 - oxapentamethylene radicals. Specified water-soluble salts are those of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury and copper; ammonium, mono-, di-, and trialkylammonium, mono-, di-, and trialkanolammonium, mixed alkylalkanolammonium and mono-, and dicycloalkylammonium salts (lists of each being specified): and salts of heterocyclic amines such as morpholine, piperidine, pyrrolidine, and hexamethyleneimine. The additional ingredient may be (1) a liquid carrier in which the active ingredient is dissolved or dispersed such as water, oils of petroleum, animal, vegetable, or synthetic origin (e.g. kerosene, fuel, lubricating, soybean, linseed, castor, sperm and cod liver oils), (2) a wetting or dispersing agent such as a fatty alcohol sulphate, an aliphatic, aromatic or alkaryl sulphonate, an alkyl polyglycolether or the anologous thioether (examples are specified) (3) a solid carrier such as a clay (e.g. fuller's earth, pyrophyllite, talc, bentonite, kieselguhr and diatomaceous earth), sulphur, volcanic ash, calcium carbonate, lime, byproduct lignin, lignocellulose, flour, e.g. from wood, walnut shell, wheat, soybean, potato and cotton seed) (4) a humectant such as glycerine, diethylene glycol, ethylene glycol, polyethylene glycols, water-soluble sugars and sugar-containing mixtures (e.g. glucose, fructose, galactose, mannose, arabinose, xylose, sucrose, maltose, lactose, raffinose and trehalose), dextrins (e.g. white dextrin, canary dextrin and British gum), honey, molasses, maple syrup, maple sugar, corn syrup and other starch syrups (5) any combination of (1), (2), (3) and (4). The resulting compositions may also include fungicides, insecticides, bactericides and other types of plant response agents. Preferred active ingredients are dimethylammonium exocis-N, N-dimethyl-, diethylammonium exocis-N, N-diethyl, and dibutylammonium exo-cis-N, N-dibutyl-3, 6-endoxohexa-hydrophthalamate, exo-cis-N, N-diethyl-, and exo-cis-N, N-diisopropyl-3, 6-endoxohexahydrophalanic acid. The examples describe (1) a dust comprising exo-cis - N - butyl - 3, 6 - endoxohexahydrophthalamic acid, talc and sodium dodecylbenzene sulphonate (2) a composition suitable for application as an aqueous dispersion comprising dimethylammonium exo - cis - N, N - dimethyl -, or butylammonium exo-cis-N-butyl-3, 6- endoxohexahydrophthalamate, fuller's earth and lignin sulphonate (3) an oil-in-water emulsion prepared by stirring an aqueous solution of exo-cis-N, N-diisopropyl-3, 6-endoxohexahydrophthalamic acid and sorbitol oleate ethylene oxide with diesel oil.
GB818853A 1951-10-31 1953-03-25 Oxygen-bridged hydrogenated derivatives of phthalamic acid Expired GB760686A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US254189A US2637644A (en) 1951-10-31 1951-10-31 Plant growth regulation
GB818853A GB760686A (en) 1953-03-25 1953-03-25 Oxygen-bridged hydrogenated derivatives of phthalamic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB818853A GB760686A (en) 1953-03-25 1953-03-25 Oxygen-bridged hydrogenated derivatives of phthalamic acid

Publications (1)

Publication Number Publication Date
GB760686A true GB760686A (en) 1956-11-07

Family

ID=9847528

Family Applications (1)

Application Number Title Priority Date Filing Date
GB818853A Expired GB760686A (en) 1951-10-31 1953-03-25 Oxygen-bridged hydrogenated derivatives of phthalamic acid

Country Status (1)

Country Link
GB (1) GB760686A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1468747B1 (en) * 1961-02-16 1970-10-15 Uniroyal Inc N-dimethylaminohexahydrophthalamic acid, -1,2,3,6-tetrahydrophthalamic acid, -3,6-endoxo-delta? -Tetrahydrophthalamic acid and -3,6-endomethylene-delta? -Tetrahydrophthalamic acid, their salts and imides
EP0248435A1 (en) * 1986-06-04 1987-12-09 E.R. Squibb &amp; Sons, Inc. Process for preparing 7-oxabicycloheptane amino-alcohol intermediates useful in making thromboxane A2 receptor antagonists and novel intermediates produced therein

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1468747B1 (en) * 1961-02-16 1970-10-15 Uniroyal Inc N-dimethylaminohexahydrophthalamic acid, -1,2,3,6-tetrahydrophthalamic acid, -3,6-endoxo-delta? -Tetrahydrophthalamic acid and -3,6-endomethylene-delta? -Tetrahydrophthalamic acid, their salts and imides
EP0248435A1 (en) * 1986-06-04 1987-12-09 E.R. Squibb &amp; Sons, Inc. Process for preparing 7-oxabicycloheptane amino-alcohol intermediates useful in making thromboxane A2 receptor antagonists and novel intermediates produced therein

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