IE53978B1 - Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group - Google Patents

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group

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Publication number
IE53978B1
IE53978B1 IE1786/82A IE178682A IE53978B1 IE 53978 B1 IE53978 B1 IE 53978B1 IE 1786/82 A IE1786/82 A IE 1786/82A IE 178682 A IE178682 A IE 178682A IE 53978 B1 IE53978 B1 IE 53978B1
Authority
IE
Ireland
Prior art keywords
process according
group
formula
alkyl
carbon atoms
Prior art date
Application number
IE1786/82A
Other versions
IE821786L (en
Original Assignee
Rhone Poulenc Agrochimie
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 Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie
Publication of IE821786L publication Critical patent/IE821786L/en
Publication of IE53978B1 publication Critical patent/IE53978B1/en

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    • 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
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • 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
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C301/00—Esters of sulfurous acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a carbon atom
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
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    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
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    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
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    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
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    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
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    • 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
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    • C07D213/60—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 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
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    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
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    • C07D333/34—Sulfur atoms
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

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  • Agronomy & Crop Science (AREA)
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Abstract

Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group, by reacting an appropriate phenoxy benzoic acid halide with a sulphonamide in the absence of an acid acceptor and with elimination of hydrohalic acid in the gaseous form.

Description

k. DESCRIPTION Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group The present invention relates to an improved process for the preparation of certain phenoxybenzoic acid derivatives containing a sulphonamide group, which have herbicidal properties.
Herbicidal derivatives of phenoxybenzoic acids containing a sulphonamide group are known from European Patent Application £33^2 Ortd fotesit NO. ΙμΊ7Ο% These patent applications disclose products of the formula: and their salts, in which formula: A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N=NCF3, POgHg or an alkyl ester thereof having 1 to 4 carbon atoms, NHg, NHOH, Ng, a carboxy group or one of its functional derivatives, a monoalkylamino or dialkylamino group, a group NH-CO-R^, in which is an alkyl, alkoxy, monoalkyl amino or dialkylamino p radical, an alkyl group, trialkylammonio, NHSOgR , in *' 2 which R is an alkyl or phenyl radical, NHCONHSOgR , in which R is as hereinbefore defined; alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylsulphonio, cyano5 39 7 8 - 2 sulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substituted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF^, -N=N-P(OCH,)- or acyl: J z B is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CF3, NO2, CN, NH2, NHCOR1, in which R^ is as hereinbefore defined, or C0NH2; C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group; D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogenoalkyl, preferably CF3, sulphamoyl, formyl, alkylcarbonyl, CN or dimethylamino group; E is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, preferably CF3< NH2, C0NH2 or NH-CO-R^, wherein is as hereinbefore defined; F is as hereinbefore defined for B; and 4 3 R is a group -CON(R )SO2R , in which: » R is hydrogen or an alkyl group having 1 to 4 carbon atoms, and 3 R is a phenyl, pyridyl or thienyl group optionally substituted by one or more halogen atoms, alkyl groups or nitro groups, an alkenyl or alkynyl radical having 2 to 4 carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine, chlorine, bromine or iodine atoms, 53878 - 3 preferably CF^, or by one or more of the following substituents: carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, roonoalkylcarbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio, alkylsulphinyl, alkylsulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 carbon atoms, alkylcarbonylamino having 2 to 5 carbon atoms, or cyano.
In the above definitions, where reference is made to alkyl radicals or radicals containing one or more alkyl groups, for example mono- and di-alkylamino, or alkoxy, the alkyl radical may be for example a lower alkyl radical having for example 1 to 6 carbon atoms.
In the known processes, the products of the formula (I) are prepared by reacting an intermediate acid halide of the formula: wherein X is chlorine, bromine or iodine and A, B, C, D, E and F are as hereinbefore defined, with a sulphonamide of the formula: , rjso2nh2 (III) wherein R3 is as hereinbefore defined, at from 25 to 14O°C, in the presence of an acid acceptor, in particular a tertiary amine, such as Ν,Ν-dimethylaniline or pyridine, an alkali metal carbonate, such as anhydrous potassium carbonate, or an alkali metal fluoride, such as caesium fluoride. - 4 The compounds of formula (I) in which R^ is hydrogen can be alkylated in a known manner, e.g. by reaction with a diazoalkane having 1 to 4 carbon atoms, so Zl as to give the corresponding products m which R is an alkyl group having 1 to 4 carbon atoms.
The compounds of formula I in which, for example, R^ is a hydrogen atom are acids and form salts with bases: such compounds may be converted in known manner into their salts.
This process for the condensation of the products of formulae (XI) and (III) has a number of disadvantages: the yields are mediocre (e.g. it is possible to calculate a yield of 27% for Exanple 14 of European Patent Application 23,392 and of 9.5% for Example 34). It is now considered that it is the presence of the acid acceptor which lowers the yield by promoting a diacylation reaction. Furthermore, the use of an acid acceptor makes the final products more difficult and more expensive to isolate and purify. An object of the invention is to overcome these disadvantages.
The process according to the invention conprises reacting an acid halide of formula II wherein X, A, B, c, D, E and F are as hereinbefore defined with a sulphonamide of 3 formula (III), wherein R is as hereinbefore defined, in the absence of an acid acceptor and at a tenperature at which the gaseous hydrogen halide (HCl, HBr or HI) formed during the reaction is eliminated from the reaction medium, as it is 3 5.7 8 - 5 formed, the reaction temperature being below the decomposition temperature of the product of formula (I) (i.e. the reaction is carried out at a temperature at which appreciable decomposition of the reaction product of the formula (I) does not occur) and optionally converting in kncwn manner a compound thus obtained into a salt thereof or converting in known manner a compound thus obtained therein R represents a hydrogen atom into a corresponding compound wherein R^ represents an alkyl group having 1 to 4 carbon atoms.
By virtue of the process according to the invention, substantially higher yields of sulphonamide derivatives of phenoxybenzoic acids can be obtained, e.g. yields of at least about 30% and frequently of at least about 50%, and with a much simpler method of recovering and purifying the final product than the methods of the known processes.
It is preferred to use an acid halide (preferably the chloride) of formula (II) in which A is the group NOg or a fluorine, chlorine, bromine or iodine atom, and preferably chlorine or NDg, B is a fluorine, chlorine, bromine or iodine preferably chlorine) atom, c, E and F are hydrogen and D is the group CFg. It is also preferred to use sulphonamides of formula (III) in which R3 is an alkyl group, especially CH^, or a group CFg.
The tenperature at which the process of the invention can be carried out depends, in particular, on whether either the acid halide of the formula (ii) or the 3978 - 6 sulphonamide of the formula (III) is in large excess, or on whether or not a solvent having catalytic properties is used.
The reaction may be carried out in the presence of an excess of acid halide of formula (II). If the acid halide (II) is in large excess, i.e. the molar ratio (II)/ (III) is from about 1.5 to 5, as is preferred, the acid halide (II) can serve as a solvent for the reaction and the reaction temperature can be from 80 to 200°C, but it is then preferably from 90 to 160°C.
The unreacted acid halide (II) can be recovered from the reaction medium by washing with an inert solvent, such as a hydrocarbon, in particular pentane, hexane, heptane, cyclopentane, cyclohexane, cycloheptane, benzene, toluene or xylene, a halogenated hydrocarbon, in particular chlorobenzenes, CS2, tetrahydrofuran, dioxane and the like.
When an excess of sulphonamide is used, for example when the molar ratio of the compounds (111)/(11) is from 1.5 to 5, the reaction temperature is then generally from 90 to 200°C and preferably fran 140 to 160°C. In any case, it must be at least sufficient to melt the reaction medium.
Hie excess sulphonamide (III) can be recovered from the reaction medium by washing with water or another inert solvent for this reactant (III).
The reactants can also be dissolved in an inert solvent having a boiling point above the reaction temperature, 53S78 - 7 e.g. a chlorinated or non-chlorinated liquid hydrocarbon, such as benzene, toluene, xylenes, mixtures of xylenes or cumene; the maximum reaction temperature is advantageously slightly below the boiling point of the solvent. Thus, in the case of cumene, which boils at about 153°C, the reaction is preferably carried out at from 130 to 150°C. The use of an inert solvent has the practical advantage of permitting better heat transfer in an industrial-scale process; it also makes it possible to avoid local overheating of the reaction medium.
According to another feature of the invention, a solvent is used which catalyses the reaction of the acid halide (XI) with the sulphonamide (III) to give the phenoxyhen2oylsulphonamide (I). Dimethylformamide (DMF, which boils at about 154°C) and dimethylacetamide (DMAC, which boils at about 164BC) are particularly advantageous in this respect, and their use makes it possible to use relatively low temperatures, e.g. from 80 to 120°C, preferably from 90 to 110°C, or higher temperatures slightly below the boiling point of these solvents; the reaction rate is then more rapid. It is especially preferred to carry out the reaction at a temperature from 80°C to the boiling point of the solvent, preferably at a temperature above 90°c.
The following Examples illustrate the present invention. 3 9 7 8 - 8 Example 1 Methanesulphonamide (2 g; 0.021 mol) is mixed with 5-[21-chloro-4'-(trifluoromethyl)-phenoxy]-2-nitrobenzoyl chloride (3.8 g; 0.01 mol). The mixture is heated for 20 minutes at 150°C. The hydrochloric acid is released from the reaction medium as it is formed. The medium is cooled to give a black oil, which is dissolved in aqueous sodium hydroxide solution; the solution is filtered and the filtrate is acidified with dilute HCl, which precipitates the product of the formula (IV). This gave, with a yield of 71%, a product (3.1 g) melting at 195-197°C and having an infra-red absorption band at 1,692 cm (C=0 group). This 3 3 7 8 - 9product has the formula: Cl CO-NH-SO2-CH3 (IV) I t I Example 2 Example 1 is repeated, but 250 g of acid chlor5 · ide and 130 g of methanesulphonamide are used. The reaction product is isolated directly after the mixture has cooled, by recrystallisation from isopropanol. i | This gives a yield of 64% (185 g) of the product of the | formula (IV). The structure of this product is con10 firmed by infra-red (absorption band at 1,692 cm-1) and by nuclear magnetic resonance (singlet at 3.5 ppm; multiplet at 8.07 ppm).
When applying the process of this example of European Patent Application 23,392, using pyridine as an acid acceptor, the yield was only 25%.

Claims (25)

1. · A process for the preparation of a phenoxybenzoic acid derivative containing a sulphonamide group, of the formula: •and its salts, in which formula: A is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N=HCF 3 , PO^g or an alkyl ester thereof having 1 to 4 carbon atoms, NHg, NHOH, Ng, a carboxy group or one of its functional derivatives, a monoalkylamino or dialkylamino group, a group NH-CO-R 1 , in which R 1 is an alkyl, alkoxy, monoalkylamino or dialkylamino radical, an alkyl group, tri alkylammonio, NHSOgR , in which R 2 is an alkyl or phenyl radical, NHCONHSOgR 2 , in 2 . which R is as hereinbefore defined, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylsulphonio, cyanosulphonyl, hydroxy, alkanoyloxy, alkoxy, alkoxy substituted by an alkoxycarbonyl group, SH, nitroso, -SCN, azide, CF 3 . -N=N-P(OCH 3 ) 2 or acyl; B is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CF 3 , NOg, CN, NHg, NHCOR 1 , in which R 1 is as hereinbefore defined, or CONHgi
2. A process according to claim 1, wherein the reaction is carried out in the presence of an excess of acid halide of formula (II).
3. A process according to claim 2, wherein the molar ratio of acid halide of formula (II) to sulphonamide of formula (III) is from 1.5 to 5. - 13
4. A process according to claim 2 or 3, wherein the reaction temperature is from 80 to 200’C. 5. Any one of claims 1 to 21. 5 3 9 7 8 - 15 5 3 3 7 8
5. A process according to claim 4 in which the temperature is from 90 to 160°C. 5
6. A process according to claim 1, wherein the reaction is carried out in the presence of an excess of sulphonamide.
7. A process according to claim 6, wherein the molar ratio of sulphonamide of formula (III) to acid halide
8. A process according to claim 6 or 7, wherein the reaction temperature is from 90 to 200’C. 9. , wherein the reaction is carried out in the presence of a solvent having a boiling point above the reaction tenperature.
9. A process according to claim 7 in which the tenperature is from 140 to 160°C.
10. , wherein the reaction is carried out in a solvent which 25 catalyses the reaction of the acid halide of formula II and the sulphonamide of formula III. 10 of formula (II) is from 1.5 to 5. 10 hereinbefore defined; F is as hereinbefore defined for B; and 4 3 R is a group -CON(R )SOgR , in which; R^ is hydrogen or an alkyl group having 1 to 4 carbon atoms, and
11. A process according to claim 10, wherein the solvent is a chlorinated or non-chlorinated liquid hydrocarbon - 11 C is hydrogen, fluorine, chlorine, bromine, iodine or an alkyl or dialkylamino group; D is fluorine, chlorine, bromine, iodine or an alkylthio, alkylsulphinyl, alkylsulphonyl, alkyl, halogeno5 alkyl, sulphamoyl, formyl, alkylcarbonyl, CN or dimethylamino group; E is hydrogen, fluorine, chlorine, bromine, iodine, an alkyl, alkoxy, alkylsulphinyl or alkylsulphonyl group, CN, halogenoalkyl, NHg, CONHg or NH-CO-R 1 , wherein R 1 is as
12. - 12 carbonylamino having 2 to 5 carbon atoms, or cyano, which process comprises reacting an acid halide of the formula: wherein X is a chlorine, bromine or iodine atom and A, B, C, D, E and F are as hereinbefore defined, with a sulphonamide of the formula: r 3 so 2 nh 2 (III) wherein R is as hereinbefore defined, in the absence of an acid acceptor and at a temperature at which the gaseous hydrogen halide formed during the reaction is eliminated from the reaction medium as it is formed, the reaction tenperature being below the deconposition tenperature of the product of formula (I) and optionally converting in known manner a compound thus obtained into a salt thereof or converting in known manner a eonpound thus obtained wherein R represents a 4 hydrogen atom into a corresponding eonpound wherein R represents an alkyl group having 1 to 4 carbon atoms.
13. A process according to any one of claims 1 to
14. A process according to claim 13, wherein the solvent is dimethylformamide or dimethylacetamide and the reaction temperature is from 80°C to the boiling point of the solvent.
15. A process according to claim 14, wherein the temperature is above 90°C. 15 10. A process according to any cne of claims 1 to 15 R rs a phenyl, pyridyl or thienyl group optionally substituted by one or more halogen atoms, alkyl groups or nitro groups, an alkenyl' or alkynyl radical having 2 to 4 carbon atoms, or an alkyl radical having 1 to 4 carbon atoms, which is optionally substituted by one or more fluorine,
16. A process according to any one of the preceding claims, wherein, in formulae (I) and (II), B is a fluorine, chlorine bromine or iodine atom, X is chlorine, A is the group NO 2 or a fluorine, chlorine, bromine or iodine atom, C, E and F are hydrogen and D is CF 3 ·
17. A process according to any one of the preceding claims wherein, in formulae (I) and (II), B and X are chlorine, A is chlorine or NO 2 , C, E and F are hydrogen and D is CFj,
18. A process according to any one of the preceding claims wherein in the sulphonamide of formula III, is an alkyl or CF 3 group.
19. A process according to claim 18 wherein R is methyl.
20. A process according to any one of the preceding claims wherein Cl CF. NO CO-Cl is reacted with CH 3 -SO 2 -NH 2 20 12. A process according to claim 11, wherein the solvent is cumene and wherein the reaction temperature is from 130 to 150°C. 20 chlorine, bromine or iodine atoms, or by one or more of the following substituents: carboxy, alkoxycarbonyl having 2 to 5 carbon atoms, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl, in which the alkyl groups have from 1 to 4 carbon atoms, alkoxy having 1 to 4 25 carbon atoms, alkylthio, alkylsulphinyl, alkylsulphonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxy having 2 to 5 carbon atoms, alkyl53978
21. A process according to claim 1 substantially as hereinbefore described in Example 1 or 2.
22. A phenoxybenzoic acid derivative of formula (I) or a salt thereof, when prepared by a process according to
23. A phenoxybenzoic acid derivative according to claim 22 of the formula
24. A process substantially as described herein with reference to the examples.
25. A phenoxybenzoic acid derivative whenever prepared by a process substantially as described herein with reference to the examples.
IE1786/82A 1981-07-27 1982-07-26 Process for the preparation of phenoxybenzoic acid derivatives containing a sulphonamide group IE53978B1 (en)

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