WO2008140338A4 - New ionic pairs with (4-chloro-2-methylphenoxy)acetate and their syntheses - Google Patents

New ionic pairs with (4-chloro-2-methylphenoxy)acetate and their syntheses Download PDF

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Publication number
WO2008140338A4
WO2008140338A4 PCT/PL2008/000035 PL2008000035W WO2008140338A4 WO 2008140338 A4 WO2008140338 A4 WO 2008140338A4 PL 2008000035 W PL2008000035 W PL 2008000035W WO 2008140338 A4 WO2008140338 A4 WO 2008140338A4
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WO
WIPO (PCT)
Prior art keywords
formula
cation
carbon atoms
methylphenoxy
chloro
Prior art date
Application number
PCT/PL2008/000035
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French (fr)
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WO2008140338A1 (en
Inventor
Juliusz Pernak
Tadeusz Praczyk
Dominika Janiszewska
Miroslaw Urbanek
Regina Gnatek
Barbara Lorys
Jan Kloczko
Janusz Pec
Original Assignee
Zaklady Chemiczne Organika Sar
Juliusz Pernak
Tadeusz Praczyk
Dominika Janiszewska
Miroslaw Urbanek
Regina Gnatek
Barbara Lorys
Jan Kloczko
Janusz Pec
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 Zaklady Chemiczne Organika Sar, Juliusz Pernak, Tadeusz Praczyk, Dominika Janiszewska, Miroslaw Urbanek, Regina Gnatek, Barbara Lorys, Jan Kloczko, Janusz Pec filed Critical Zaklady Chemiczne Organika Sar
Publication of WO2008140338A1 publication Critical patent/WO2008140338A1/en
Publication of WO2008140338A4 publication Critical patent/WO2008140338A4/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/16—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms

Abstract

New ionic pairs contain (4-chloro-2-methylphenoxy)acetate anion of the general formula 1, in which K means ammonium cation of the formula 2 or 3 or 4 or 5 or 6, or pyridinium cation of the formula 7, or imidazolium cation of formula 8, or morpholinium cation of the formula 9, or piperidinium cation of the formula 10, or 8-hydroxyquinolinium cation of the formula 11, or pyrazolium cation of the formula 12, or 2-chloroethylmethylammonium cation of the formula 13, or pyrolidinium cation of the formula 14, where R means alkyl linear chain group containing 1 to 18 carbon atoms or mixture of linear alkyl chains from 1 to 20 carbon atoms (common names cocalkyl or hydrogenated tallowalkyl) or polyoxyethylene chain. New compounds are obtained in the exchange reaction between chloride or bromide salts of K cation of specified formula and (4-chloro-2-methylphenoxy)acetic acid in presence of sodium or potassium salts used at molar ratio 1 : (from 0.8 to 3) : (from 0.8 to 4) at temperature from 273 to 373K in aqueous medium or organic solvent, followed by product isolation.

Claims

AMENDED CLAIMS received by the International Bureau on 09December 2008 (09.12.08)What is claimed is:
1. New ionic pairs containing (4-chloro-2-methylphenoxy)acetate anion of the general formula 1, in which K means ammonium cation of the formula 2 or 3 or 4 or 5 or 6, or pyridinium cation of the formula 7, or imidazolium cation of formula 8, or morpholinium cation of the formula 9, or piperidinium cation of the formula 10, or 8- hydroxyquinolinium cation of the formula 11, or 2-chloroethylmethylarnmonium cation of the formula 12, or pyrolidinium cation of the formula 13, where R means alkyl linear chain group containing 1 to 18 carbon atoms or mixture of linear alkyl chains from 1 to 20 carbon atoms (common names cocalkyl or hydrogenated tallowalkyl) or polyoxyethylene chain.
2. The method of synthesis of new ionic pairs containing (4-chloro-2- methylphenoxy)acetate anion of the general formula 1, in which K means ammonium cation of the formula 2 or 3 or 4 or 5 or 6, or pyridinium cation of the formula 7, or imidazolium cation of formula 8, or morpholinium cation of the formula 9, or piperidinium cation of the formula 10, or 8-hydroxyquinolinium cation of the formula 11, or 2- chloroethylmethylamrnonium cation of the formula 12, or pyrolidinium cation of the formula 13, where R means alkyl linear chain group containing 1 to 18 carbon atoms or mixture of linear alkyl chains from 1 to 20 carbon atoms (common names cocalkyl or hydrogenated tallowalkyl) or polyoxyethylene chain, characteristic of the method of synthesis based on the exchange reaction between chloride or bromide salt of ammonium cation of the formula 2 or 3 or 4 or 5 or 6, or pyridinium cation of the formula 7, or imidazolium cation of formula 8, or morpholinium cation of the formula 9, or piperidinium cation of the formula 10, or 8-hydroxyquinolinium cation of the formula 11, or 2- chloroethylmethylammonium cation of the formula 12, or pyrolidinium cation of the formula 13, where R means alkyl linear chain group containing 1 to 18 carbon atoms or mixture of linear alkyl chains from 1 to 20 carbon atoms (common names cocalkyl or hydrogenated tallowalkyl) or polyoxyethylene chain, undergoes the exchange with (4-chloro2-methylphenoxy)acetic acid in presence of sodium or potassium hydroxide used at molar ratio 1 : (from 0.8 to 3) : (from 0.8 to 4) at temperature from 273 to 373K in aqueous medium or organic solvent, followed by product isolation.
3 . The method as in point 2, characteristic of removal of water followed by drying of product.
4. The method as in point 2, characteristic of removal of organic solvent, addition of chloroform or ethyl acetate, separation of organic phase and isolation of product by evaporation the introduced solvent under reduced pressure.
PCT/PL2008/000035 2007-05-11 2008-05-08 New ionic pairs with (4-chloro-2-methylphenoxy)acetate and their syntheses WO2008140338A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PL382404A PL382404A1 (en) 2007-05-11 2007-05-11 New ionic vapours comprising (4-chloro-2-methylphenoxy)acetic anion and methods for production thereof
PLP382404 2007-05-11

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WO2008140338A1 WO2008140338A1 (en) 2008-11-20
WO2008140338A4 true WO2008140338A4 (en) 2009-03-05

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WO (1) WO2008140338A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2775833B1 (en) * 2011-11-07 2017-10-04 Bayer Intellectual Property GmbH Use of ionic compounds for controlling glyphosate resistent plants
DK2880978T3 (en) * 2013-12-09 2018-01-08 Przed Produkcyjno-Consultingowe Adob Sp Z O O Sp K Herbicidal quaternary ammonium salts of (4-chloro-2-methylphenoxy) acetic acid
ES2689516T3 (en) 2015-05-13 2018-11-14 Przedsiebiorstwo Produkcyjno-Consultingowe Adob Sp. Z O.O. Sp. K. Ionic liquids herbicide with cation type betaine
PL237908B1 (en) * 2018-02-01 2021-06-14 Przed Produkcyjno Consultingowe Adob Spolka Z Ograniczona Odpowiedzialnoscia Spolka Komandytowa Herbicidal ionic liquid with 4-chloro-2-methylphenoxyacetic acid anion and eutectic mixture containing it

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* Cited by examiner, † Cited by third party
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CA1049536A (en) * 1972-11-17 1979-02-27 Richard W. Feeny Herbicidal compositions
US4170464A (en) * 1974-10-25 1979-10-09 American Cyanamid Company Herbicidal combinations

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PL382404A1 (en) 2008-11-24

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