JPS5826860A - Manufacture of phenoxybenzoic acid derivative containing sulfonamide group - Google Patents

Manufacture of phenoxybenzoic acid derivative containing sulfonamide group

Info

Publication number
JPS5826860A
JPS5826860A JP57130216A JP13021682A JPS5826860A JP S5826860 A JPS5826860 A JP S5826860A JP 57130216 A JP57130216 A JP 57130216A JP 13021682 A JP13021682 A JP 13021682A JP S5826860 A JPS5826860 A JP S5826860A
Authority
JP
Japan
Prior art keywords
group
formula
reaction
carbon atoms
alkyl
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.)
Granted
Application number
JP57130216A
Other languages
Japanese (ja)
Other versions
JPH0149262B2 (en
Inventor
エル−アマデイ・アイ・ヘイバ
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.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
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 SA filed Critical Rhone Poulenc Agrochimie SA
Publication of JPS5826860A publication Critical patent/JPS5826860A/en
Publication of JPH0149262B2 publication Critical patent/JPH0149262B2/ja
Granted legal-status Critical Current

Links

Classifications

    • 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
    • A01N1/00—Preservation of bodies of humans or animals, or parts 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
    • 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
    • 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
    • C07C311/15—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
    • 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
    • C07C311/51—Y being a hydrogen or a carbon atom
    • 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
    • C07C311/50—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C07C323/23—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
    • 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
    • C07C323/23—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
    • 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
    • C07C323/23—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
    • 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
    • C07C323/50—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
    • 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
    • C07C323/64—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
    • 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
    • C07C323/64—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • 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
    • 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
    • C07C63/04—Monocyclic monocarboxylic acids
    • C07C63/06—Benzoic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • 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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—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
    • 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • 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 System
    • 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 System
    • 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 System
    • 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 System
    • 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, i.e. RP(=X)(XH)2 (X = S, Se)
    • 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 System
    • 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, i.e. RP(=X)(XH)2 (X = S, 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

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 本発明は、除草性を有するスルホンアミド基を含んだ載
る朴のフェノキシ安息看酸訪導体の改良製造方法に関；
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an improved method for producing a phenoxybenzoic acid derivative containing a sulfonamide group having herbicidal properties;
It is something to do.

スルホンアミド基を有するフェノキシ安息香酸の除琴性
誘導体は、ヨーロッパ牲許出顧第３，４１６号および２
３，３９２号各明細書から公知である。Chryptolytic derivatives of phenoxybenzoic acid having a sulfonamide group are disclosed in European Patent Application Nos. 3,416 and 2.
It is known from the specifications of No. 3,392.

これらの特許出願明細書は、式 〔上記式中人は水素、弗素、塩素、臭素、沃素、ニトロ
基、−Ｎ”ＮＣＦｓ＋　ＰＯｓＨｓおよび１〜４個の炭
素原子を有するそのアルキルエステル基、ＭｉＮＨＯＨ
，＜、カルボキシル基もしくは゛その官能性誘導基のｌ
ｓ１モノアルキルアミノもしくはジアルキルアミノ基、
基ＮＨ−ＣＯ−Ｒ”　（ここで　Ｒ１はアルキル、アル
コキシ、モノアルキルアミノｌはアルキルまたはフェニ
ル基である）、ＮＨｃｏＮＨｓへｒ　（ここで、Ｐは上
記の意味を有する）、アルキルチオ、アルキルスルフィ
ニル、アルキルスルホニル、ジアルキルスルホニオ、シ
アノスルホニル、ヒト四キシ、アルカノイルオキシ、ア
ルコキシ、アルコキシカルボニルで置換され九アルコキ
シ、８Ｈ，ニトロソ、−８ＣＮ。These patent applications are based on the formula [wherein the above formula is hydrogen, fluorine, chlorine, bromine, iodine, a nitro group, -N''NCFs+ POsHs and its alkyl ester group having 1 to 4 carbon atoms, MiNHOH]
,<, carboxyl group or its functional derivative l
s1 monoalkylamino or dialkylamino group,
the group NH-CO-R'' (where R1 is alkyl, alkoxy, monoalkylamino l is an alkyl or phenyl group), NHcoNHs (where P has the above meaning), alkylthio, alkylsulfinyl, Alkylsulfonyl, dialkylsulfonio, cyanosulfonyl, human tetraxy, alkanoyloxy, alkoxy, nine alkoxy substituted with alkoxycarbonyl, 8H, nitroso, -8CN.

であ如、　　　　　　。Denyo, 　　　　.

Ｂ灯水素、弗素、塩素、臭素、沃素、アルキル、アル；
キシ、アルキルスルフィニル４Ｌ＜はアルキルスルホニ
ル基、Ｃ１２，Ｎｏ！、　ＣＮ、　ＮＨ，ｌ。B lamp hydrogen, fluorine, chlorine, bromine, iodine, alkyl, alk;
xy, alkylsulfinyl 4L< is an alkylsulfonyl group, C12, No! , CN, NH,l.

ＮＨＣＯＲ”　（ここでＨ１ｄ上記に定款した通シであ
る）またはｃｏ幽ｆｉｂ。NHCOR” (where H1d is the agreement set out in the Articles of Incorporation above) or co-author fib.

Ｃは水素、ハロゲンまたはアルキルもしくはジアルキル
アミノ基であり、 Ｄは弗素、塩素、臭素、沃素またはＣＦｓ＋アルキルチ
オ、アルキルスルフィニル、アルキルスルホニル、ハロ
ゲンアルキル、スルファモイル、ホルミル、アルキルカ
ルボニル、ＣＮまたハシメチルアミノ基であυ、 五は水素、ハロゲンアルキル、アルコキシ、アルキルス
ルフィニルまたれアルキルスルホニル基、ＣＮＩ　ＯＦ
、、　１％、　ＣＯ隅またはＮＨベトＲ１（ここでＢ１
１１上記の意味を有する）でｉｂ、ＦはＢについ゛て示
した意味の１つを有し、Ｒは基−ＣＯＮ（Ｒ’）毅５で
あル、ここでｔは水素または１〜４個の炭素原子を有す
るアルキル基であシ、 Ｒａけフェニル、ピリジルまたはチェニル基（これらの
基は任意的に、１個もしくはそれ以上のハロゲン原子、
アルキル基もしくはニトロ基によ多置換されていてもよ
い）、２〜４個の炭素原子を有するアルケニルもしくは
アルキニル基、または１〜４個の炭素原子を有するアル
キル基（任意的に、１個もしくはそれ以上の弗素、塩素
、臭素もしくは沃素原子、好ましくはＣＦ３により置換
されていてもよく、または１個屯しくけそれ以上の次の
置換基により置換されていてもよい：カルボキシル、２
〜５個の炭素原子を有するアルコキシカルボニル、２〜
５個の炭素原子を有するアルキルカルボニル、アルキル
部分が１〜４個の炭素原子を有するモノアルキルカルバ
モイルもしくハシアルキルカルバモイル、それぞれ１〜
４個の炭素原子を有するアルキルチオ、アルキルスルフ
ィニル、アルキルスルホニル、２〜５個の炭素原子を有
するアルキルカルボニルオキシ、２〜５個の炭素原子を
有スるアルキルカルボニルアミノ甘たはシアノ基〕 の化合物とその塩とを開示している。C is hydrogen, halogen or an alkyl or dialkylamino group; D is fluorine, chlorine, bromine, iodine or CFs+alkylthio, alkylsulfinyl, alkylsulfonyl, halogenalkyl, sulfamoyl, formyl, alkylcarbonyl, CN or a hashimethylamino group; Aυ, 5 is hydrogen, halogen alkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CNI OF
,, 1%, CO corner or NH bet R1 (here B1
11 with the meaning given above), F has one of the meanings given for B, R is the group -CON(R'), where t is hydrogen or 1-4 an alkyl group having 1 or more carbon atoms, a phenyl, pyridyl or chenyl group, which optionally contains one or more halogen atoms,
an alkenyl or alkynyl group having 2 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (optionally one or more It may be substituted by more fluorine, chlorine, bromine or iodine atoms, preferably CF3, or by one or more of the following substituents: carboxyl, 2
~alkoxycarbonyl having 5 carbon atoms, 2~
alkylcarbonyl having 5 carbon atoms, monoalkylcarbamoyl or hasialkylcarbamoyl in which the alkyl moiety has 1 to 4 carbon atoms, respectively 1 to 4 carbon atoms;
Compounds of alkylthio having 4 carbon atoms, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy having 2 to 5 carbon atoms, alkylcarbonylamino sweet or cyano group having 2 to 5 carbon atoms and its salt.

公知方法においては、式（１）の化合物は、式〔式中、
ｘＨ塩素、臭素もしくは沃素であり、Ａ、Ｂ、Ｃ，Ｄ、
ＥおよびＦは上記の意味を有する〕 の中間体の蒙ノ・ロゲン化物を式 ％式％（２） 〔式中、では上記の意味を有する〕 のスルホンアミドと２５〜１４０℃の温度にて酸受容体
の存在下、特にたとえばＮ、Ｎ−７／メチルアニリンも
しく祉ピリジンのような第３級アきン、たとえに無水炭
酸カリウムのようなアルカリ金属巌酸塩、またはたとえ
ば弗化セシウムのよう表アルカリ金島弗化物の存在下で
反応させることによシ製造することができる。In known methods, the compound of formula (1) is prepared from the formula [wherein,
xH chlorine, bromine or iodine, A, B, C, D,
E and F have the above meanings] The intermediate monologenide of the formula % (2) [wherein has the above meanings] is mixed with the sulfonamide of the formula % (2) [wherein has the above meanings] at a temperature of 25 to 140°C. In the presence of an acid acceptor, especially a tertiary amine such as N, N-7/methylaniline or pyridine, an alkali metal salt such as anhydrous potassium carbonate, or e.g. cesium fluoride. It can be produced by reacting in the presence of an alkali Kanajima fluoride.

ｔが水素原子である式（１）の化合物は、公知方法によ
シたとえば１〜４個のＪｉ２素原子を有するジアゾアル
カンとの反応によジアルキル化して、ｔが１〜４個の炭
素原子を有するアルキル基である対応する化合物を生成
させることができる。Compounds of formula (1) in which t is a hydrogen atom can be dialkylated by known methods, for example by reaction with a diazoalkane having 1 to 4 Ji2 atoms, to form compounds in which t is 1 to 4 carbon atoms. Corresponding compounds can be generated that are alkyl groups with .

式（…）の化合物と式（２）の化合物との縮合に関する
この方法は多くの欠点を有する。たとえば、収率が好ま
しくない（たとえば、ヨーロッパ特許出願第２３．８９
２号の実施例１４については収率が２７チであり、また
実施例３４について社収率９．５％と算定できる）。ジ
アシル化反応の促進によシ収率が低下するのであるか、
その主な原因は酸受容体の存在であると考えられる。さ
らに、酸受容体の使用により最終生成物の単離および精
製がより困難になり、かつその費用も一層高価になるＣ 本発明の一目的は、これらの欠点を克服することである
。This method for the condensation of compounds of formula (...) with compounds of formula (2) has a number of drawbacks. For example, the yield is unfavorable (e.g. European Patent Application No. 23.89
For Example 14 of No. 2, the yield is 27%, and for Example 34, the company yield can be calculated as 9.5%). Is it because the acceleration of the diacylation reaction reduces the yield?
The main cause is thought to be the presence of acid receptors. Furthermore, the use of acid acceptors makes the isolation and purification of the final product more difficult and more expensive. One aim of the present invention is to overcome these drawbacks.

本発明による方法は、酸ハロゲン化物（好ましくは塩化
物、臭化物または沃化物）を、酸受容体の不存在下、か
つハロゲン化水素酸（ＨＣＬ、　ＨＢｒ。The process according to the invention comprises converting an acid halide (preferably a chloride, bromide or iodide) in the absence of an acid acceptor and into a hydrohalic acid (HCL, HBr).

ＨＩ）が生成されるそばから気体として反応媒体よシ除
去されるような温度、シかも式（１）の反応生成物の°
′認めうる分解”を伴なわないような温度にて、式（２
）のスルホ／アミドと反応させることを特徴とする。The temperature of the reaction product of formula (1) is such that HI) is removed from the reaction medium as a gas from where it is formed.
At a temperature that does not involve any appreciable decomposition, the formula (2
) with a sulfo/amide.

本発明の方法によれは、フェノキシ安息香酸のスルホン
アミド誘導体が相当に高い収率で得ることができ、たと
えば、少なくとも約３０％しはしば少なくとも約５０％
という収率で得られ、しかも最終生成物の回収および精
製操作Ｌ１公知方法の場合よりもずっと簡単である。According to the process of the invention, sulfonamide derivatives of phenoxybenzoic acid can be obtained in considerably high yields, for example at least about 30% and often at least about 50%.
However, the final product recovery and purification operations L1 are much simpler than in the known method.

実際上、本発明に使用する酸ハロゲン化物は式（Ｉｔ）
の酸ハロゲン化物である。Ａが基ＮＯＩまたは弗素、塩
素、臭棄もしくは沃素原子であり、Ｂがハロゲン原子で
あり、Ｃ，ＥおよびＦが水素原子であシかつＤが基ＣＦ
、であるような式のハロゲン化物を使用するのが好適で
ある。さらに、Ｒｓがアルキル基、特にＣＨ３または基
ＣＦＩであるような式（４）のスルホンアミドを使用す
るのも好適である３、本発明の方法を行ないうる温度は
、特に式（ＩＩ）の酸ハロゲン化物または式（至）のス
ルホンアミドのいずれかが大過剰に存在するかどうか、
或いは触媒特性を有する溶剤を使用するかしないかに依
存して、種々変わるであろう。In practice, the acid halide used in the present invention has the formula (It)
It is an acid halide. A is a group NOI or a fluorine, chlorine, odorant or iodine atom, B is a halogen atom, C, E and F are hydrogen atoms and D is a group CF
It is preferred to use halides of the formula. Furthermore, it is also suitable to use sulfonamides of the formula (4) in which Rs is an alkyl group, in particular a CH3 or a group CFI. whether either the halide or the sulfonamide of formula is present in large excess;
Alternatively, it will vary depending on whether a solvent with catalytic properties is used or not.

たとえば、酸ハロゲン化物（ＩＩ）が大過剰に存在する
場合、すなわち（Ｉ）／（２）のモル比が約１．５〜５
の範囲である場合、この酸ハロゲン化物（ＩＩ）は反応
用溶媒として役立たせることができ、反応温度を８０〜
２００℃とすることができるが、好ましくは９０〜１６
０℃の範囲である。For example, when the acid halide (II) is present in large excess, i.e. the molar ratio of (I)/(2) is about 1.5-5
When the acid halide (II) is in the range of
It can be 200°C, but preferably 90-16
It is in the range of 0°C.

未反応のハロゲン化物（１）は、これを不活性溶剤たと
えば炭化水素、特にペンタン、ヘキサン、ヘプタン、シ
クロペンタン、シクロヘキサン、シクロヘプタン、ベン
ゼン、トルエン４Ｌ＜ｔｉキシレン、ハロゲン化炭化水
素、特にクロルベンゼン、ＣＳ、、テトラヒドロ７ラン
、ジオキサンなどで洗浄するごとによｐ反応媒体から回
収することができるＯ 過剰量のスルホンアミドを使用する場合、すなわち化合
物（４）／（Ｉ）のモル比が１．５〜５の範囲である場
合、反応温度は一般に９０〜２００℃、好ましくは１４
０〜１６０℃である０いずれの場合において・も、反応
温度は、少なくとも反応媒体を溶融させるのに充分なＩ
ｔ度でなけれにならない０過剰のスルホンアミド（２）
は、これを水またはこの反応体（２）に対して不活性な
他の溶剤によル洗浄して反応媒体から回収することがで
きる。The unreacted halide (1) can be washed with an inert solvent such as a hydrocarbon, especially pentane, hexane, heptane, cyclopentane, cyclohexane, cycloheptane, benzene, toluene, xylene, a halogenated hydrocarbon, especially chlorobenzene. , CS, , tetrahydro7ran, dioxane, etc. can be recovered from the reaction medium by each washing with O. .5 to 5, the reaction temperature is generally 90 to 200°C, preferably 14
In each case, the reaction temperature is between 0 and 160°C, at least enough to melt the reaction medium.
0 excess of sulfonamide (2) which must be at t degrees
can be recovered from the reaction medium by washing with water or other solvents inert towards the reactant (2).

さらに、反応体は反応温度より高い沸点を有する不活性
溶剤、たとえば塩素化もしくは非塩素化液体炭ｆ化水素
、たとえばベンゼン、トルエン、キシレン、キシレンの
混合物またはクメンに溶解させることもでき、この場合
、最高反応温度は溶剤の沸点よりわずか低くするのが有
利である。たとえば、沸点が約１５３℃であるクメンの
場合、反応は好ましくは１３０〜１５０℃で行なわれる
。Furthermore, the reactants can also be dissolved in an inert solvent with a boiling point above the reaction temperature, such as chlorinated or non-chlorinated liquid hydrocarbons, such as benzene, toluene, xylene, xylene mixtures or cumene, in which case Advantageously, the maximum reaction temperature is slightly below the boiling point of the solvent. For example, in the case of cumene, which has a boiling point of about 153°C, the reaction is preferably carried out at 130-150°C.

不活性溶剤の使用は、工業規模の方法において一層良好
な熱移動を可能にするという実用的利点を有する。さら
に、これは反応媒体の局部的過熱の防止にも役立つ＠ 本発明の他の具体例によれば、酸ハロゲン化物（１）と
スルホンアミド（２）との反応によジフェノキシベンゾ
イルスルホンアミド（１）を生成させるための触媒作用
を有する溶剤が使用される０この点でジメチルホルムア
ミド（−ＤＭＦ、　　これは約１５４℃で沸とうする）
およびジメチルアセトアミド（−ＤＭＡＣ，これは約１
６４℃で沸とうする）が特に有利であル、それらの使用
によシ、反応を比較的低い温度、たとえば８０〜１２０
℃、好ましくは９０〜１１０℃の温度、或いはこれら溶
剤の沸点よシ僅かに低い温度において実施できるように
な）、かつ、反応速度はよシ高速となる。The use of inert solvents has the practical advantage of allowing better heat transfer in industrial scale processes. Furthermore, this also serves to prevent local overheating of the reaction medium. According to another embodiment of the invention, the reaction of acid halide (1) with sulfonamide (2) produces diphenoxybenzoylsulfonamide ( 1) A catalytic solvent is used to produce dimethylformamide (-DMF, which boils at about 154°C).
and dimethylacetamide (-DMAC, which is approximately 1
(boiling at 64°C) are particularly advantageous; their use allows the reaction to be carried out at relatively low temperatures, e.g.
C, preferably from 90 to 110 C, or slightly below the boiling point of these solvents), and the reaction rate is much faster.

以下、実施例により本発明を説明しかつどのように実施
されうるかを具体的に示すが、本発−〇範囲はこれによ
シ限定されるものでない。EXAMPLES Hereinafter, the present invention will be explained with reference to examples and how it can be carried out will be specifically shown, but the scope of the present invention is not limited thereto.

！上皇ユ メタンスルホンアミ）”（ｚｇ、０．０２１モル）を５
−（２’−クロル−４’−（）リフルオロメチル）−フ
ェノキシフ−２−二トローベンゾイルクロライド（３，
８ｇ、　ｏ、ｏ　１モル）と混合した。この混合物を１
５０℃にて２０分間加熱した。塩酸を、生成されるそば
から反応媒体より放出させた。この媒体を冷却して黒色
油状物を得、これを水酸化ナトリウム水溶液中に溶解し
た。この溶液を濾過しそしてｐ液を希塩酸で酸性化させ
、これによシ式（転）の生成物を沈澱させた。かくして
、収率７１チをもって、１９５〜１９７℃にて溶融しが
っ１．６９２ｃｒｎ″″’（Ｃ−０基）に赤外吸収帯を
有する生成物（３，ｔｇ）が得られた。仁の生成物は式
実施例１を反復したが、この場合２５０ｇの酸塩化物と
１３０ｇのメタンスルホンアミドとヲ使用した。反応生
成物は、混合物を冷却した後にイングロパノールからの
再結晶によシ直接に単離し九〇これによシ、式（転）の
生成物が収率６４％（１８１ｇ）で得られた。この生成
物の構造は、赤外吸収スペクトル（１，６９２ｅｍ−’
における吸収帯）および核磁気共鳴スペクトル（ａ、ｓ
ｐ−にてシングレット、８．０７　ｐｐｍにてマルチプ
レット）Ｋよシ確諺された。! Retired Emperor Yumetane Sulfonamide)” (zg, 0.021 mol) 5
-(2'-chloro-4'-()lifluoromethyl)-phenoxif-2-nitrobenzoyl chloride (3,
8 g, o, o 1 mol). 1 of this mixture
Heated at 50°C for 20 minutes. Hydrochloric acid was released from the reaction medium from the buckwheat produced. The medium was cooled to give a black oil, which was dissolved in aqueous sodium hydroxide solution. The solution was filtered and the p-liquid was acidified with dilute hydrochloric acid, thereby precipitating the product of the formula. Thus, a product (3,tg) was obtained with a yield of 71 cm, which melts at 195-197 DEG C. and has an infrared absorption band at 1.692 crn'''' (C-0 group). For the product, formula Example 1 was repeated, but in this case 250 g of acid chloride and 130 g of methanesulfonamide were used. The reaction product was directly isolated by recrystallization from ingropanol after cooling the mixture. This gave the product of formula (conversion) in 64% yield (181 g). . The structure of this product is shown in the infrared absorption spectrum (1,692 em-'
absorption bands) and nuclear magnetic resonance spectra (a, s
Singlet at p-, multiplet at 8.07 ppm) confirmed by K.

比較のために、ヨーロッパ特許出願第２３．３９２号の
実施例に記載の方法を使用し、ピリジンを酸受容体とし
て使用して反応を行った場合、収率は僅か２５％でちっ
た。For comparison, when the reaction was carried out using the method described in the Examples of European Patent Application No. 23.392 and using pyridine as the acid acceptor, the yield was only 25%.

代理人斧珊士今　　村　　　　元Agent Ax Sanshi Imamura Moto

Claims (1)

【特許請求の範囲】 （１１式 〔式中、人は水素、弗素、塩素、臭素、沃素。 ニトロ基＋　　Ｎ＝ＮＣＦｇ　ｒ　ＰＯｎ　＆および１
〜４個の炭素原子を有するそのアルキルエステル基、Ｍ
Ｈｓ　、　ＮＨＯＨ−Ｎ黛、カルボキシル基もしくはそ
の一官能性誘導基の１種、モノアルキルアミノもしくは
ジアルキルアミン基、基ＮＨ−ＣＯ−Ｒ’（ここで、Ｗ
はアルキル、アルコキシ、モノアルキルこで、Ｒ３はア
ルキルまたはフェニル基である）、ＮＨＣＯＮＨ８０，
Ｒ”　（ここで、Ｗは上記の意味を有すル）、アルキル
チオ、アルキルスルフィニル、アルキルスルホニル、ジ
アルキルスルホニオ、シアノスルホニル、ヒドロキシル
、アルカノイルオキシ、アルコキシ、アルコキシカルボ
ニルで置換されたアルコキシ、ＳＨ，ニトロソ、−８Ｃ
Ｎ。 あり、　　　　　　　　。 Ｂは水素、弗素、塩素、臭素、沃素、アルキル、アルコ
キシ、アルキルスルフィニル４Ｌ＜はアルキルスルホニ
ル基、ｃＦ’ｓ、　ＮＯｘ＋　ＣＮ＋　ＮＨ２゜ＮＨＣ
ＯＲ’　　（ここで　Ｒ１は上記に定義した通シである
）またはＣ０ＮＨＩであシ、 Ｃは水素、ハロゲンまたはアルキルもしくはジアルキル
アミノ基であり、 Ｄは弗素、塩素、臭素、沃素またはｃＦｓ、アルキルチ
オ、アルキルスルフィニル、アルキルスルホニル、ハロ
ゲノアルキル、スルファモイル、ホルミル、アルキルカ
ルボニル、ＣＮま九はジメチル７電ノ基であシ、 Σは水素、ハロゲノアルキル、アルコキシ、アルキルス
ルフィニルまたはアルキルスルホニル基、ＣＮ、　ＣＦ
ｓ、　Ｎｕｓ、　Ｃ０ＮＨｚまたｉｆ　ＮＨ−Ｃｏ−Ｒ
”（ここで、Ｒ囃上記の意味を有する）であり、ＦはＢ
について示した意味の１つを有し、Ｒは基−ＣＯＮ（Ｒ
’）　８０ｔＲ”であシ、ここでＲ４は水素、または１
〜４個の炭素原子を有するアルキル基であシ、 Ｗはフェニル、ピリジルまたはチェニル基（これらの基
は任意的に、１個もしくはそれ以上のハロゲン原子、ア
ルキル基本しくはニトロ基によ）置換されていてもよい
）、２〜４個の炭素原子を有するアルケニルもしくはア
ルキニル基、または１〜４個の炭素原子を有するアルキ
ル基（任意的に、１個もしくはそれ以上の弗素、塩素、
臭素もしくは沃素原子、好ましくはＣＦ３により置換さ
れていてもよく、または、１個もしくはそれ以上の次の
置換基により置換されていて本よい二カルボキシル、２
〜５個の炭素原子を有するアルコキシカルボニル、２〜
５個の炭素原子を有するアルキルカルボニル、アルキル
部分が１〜４個の炭素原子を有するモノアルキルカルバ
モイル４Ｌ＜ｕジアルキルカルバモイル、それぞれ１〜
４個の炭素振４を有するアルキールチオ、アルキルスル
フィニル、アルキルスルホニル、２〜Ｉｓ個の炭素原子
を有するアルキルカルボニルオキシ、２〜５個の炭素原
子を有するアルキルカルボニルアミノまたはシアノ基〕 のスルホンアミド基を有するフェノキシ安息香酸誘導体
またはその塩を製造する方法において、〔式中、Ｘは塩
素、臭素もしくは沃素原子であシ、ム、Ｂ、Ｃ，Ｄ、Ｅ
およびＦ杜式（１）において上記した意味を有する〕 の酸ハロゲン化物を式 ％式％ 〔式中、Ｒ−も上記の意味を有する〕 のスルホンアミドと反応させ、この反応を酸受容体の不
存在下かつ気体状水素−酸副生物が生成されるそばから
反応媒体よシ除去されるような温度にて行ない、ただし
この温度は式（１）の生成切の分解温度よシ低いことを
特徴とするスルホンアミド基を有するフェノキシ安息香
酸誘導体またはその塩の製造方法。 （２）反応を過剰量の式（Ｉｔ）の酸ハロゲン原子の存
在下で行なう特許請求の範囲第１項記載の方法。 （ａ）　　式（１）の酸ハロゲン化物／式＠）のスルホ
ンアミドのモル比を１．５〜５の範囲内とする特許請求
の範囲第２項記載の方法。 （４）反応温匿を８０〜２００℃、好ましくは９０〜１
６０℃とする特許請求の範囲第２項またはｆｇａ項記載
の方法。 （５）　　反応を過剰量のスルホンアンドの存在下で行
なう特許請求の範囲第１項記載の方法。 （６）式（転）のスルホンアミド／式（幻の酸ハロゲン
化物のモル比を１，５〜５の範囲内とする特許請求の範
囲第５項記載の方法。 （７）反応温度を９０〜２００℃、好ましくは１４０〜
１６０℃とする特許請求の範囲第５３Ａｙ九扛第６項記
載の方法。 （８）反応を、反応温度よ）高い沸点を有する溶剤の存
在下で行なう特許請求の範Ｈ第１項乃至第７項のいずれ
かに記載の方法。 （９）溶剤を炭化水素とする特許請求の範囲第８項記載
の方法。 （転）溶剤をクメンとしかつ温度を１３０〜１５０℃と
する特許請求の範囲第９項記載の方法。 （ロ）反応を、この反応に関して触媒特性を有する溶剤
の存在下で行なう特許請求の範囲第１項乃至第８項のい
ずれかに記載の方法。 （２）溶剤をジメチルホルムアミドもしくはジメチルア
セドブミドとしかつ温度を８０℃乃至溶剤の沸点の範囲
内とする特許請求の範囲第１１項記載の方法。 （至）温度を９０℃よシ高くする特許請求の範囲第１１
項記載の方法。 ０４　　式（１）および（ｎ）にふ・いて、ＢおよびＸ
が塩素原子であり、Ａが塩素原子まだはＮｏ鵞であり、
Ｃ１ＥおよびＦが水素原子であシかつＤがＣＦ３である
特許請求の範囲第１項乃至第１３項のいずれかに記載の
方法。 （２）Ｒ１がアルキルまたはＣＦ、基、好ましくはメチ
ル基であるスルホンアミドを使用する特許請求の範囲第
６項または第７項記載の方法。 （Ｌｉ２式 の化合物を式 Ｃ＆−ｓｏ、−隅 の化合物と反応させる特許請求の範囲側１項乃至第１５
項のいずれかに記載の方法◇[Claims] (Formula 11 [In the formula, hydrogen is hydrogen, fluorine, chlorine, bromine, iodine. Nitro group + N=NCFg r POn & and 1
its alkyl ester group having ~4 carbon atoms, M
Hs, NHOH-N, a carboxyl group or one of its monofunctional derivatives, a monoalkylamino or dialkylamine group, a group NH-CO-R' (where W
is alkyl, alkoxy, monoalkyl, and R3 is an alkyl or phenyl group), NHCONH80,
R” (wherein W has the above meaning), alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonio, cyanosulfonyl, hydroxyl, alkanoyloxy, alkoxy, alkoxy substituted with alkoxycarbonyl, SH, nitroso , -8C
N. can be, . B is hydrogen, fluorine, chlorine, bromine, iodine, alkyl, alkoxy, alkylsulfinyl 4L< is an alkylsulfonyl group, cF's, NOx+ CN+ NH2゜NHC
OR' (where R1 is a group as defined above) or CONHI, C is hydrogen, halogen or an alkyl or dialkylamino group, D is fluorine, chlorine, bromine, iodine or cFs, alkylthio, Alkylsulfinyl, alkylsulfonyl, halogenoalkyl, sulfamoyl, formyl, alkylcarbonyl, CN and 9 are dimethyl heptaelectron groups, Σ is hydrogen, halogenoalkyl, alkoxy, alkylsulfinyl or alkylsulfonyl groups, CN, CF
s, Nus, C0NHz or if NH-Co-R
” (here, R music has the above meaning), and F is B
has one of the meanings indicated for R and R is the group -CON(R
') 80tR'', where R4 is hydrogen or 1
is an alkyl group having ~4 carbon atoms, W is a phenyl, pyridyl or chenyl group (optionally substituted by one or more halogen atoms, an alkyl group or a nitro group) ), an alkenyl or alkynyl group having 2 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (optionally one or more fluorine, chlorine,
dicarboxyl optionally substituted by a bromine or iodine atom, preferably CF3, or substituted by one or more of the following substituents, 2
~alkoxycarbonyl having 5 carbon atoms, 2~
alkylcarbonyl having 5 carbon atoms, monoalkylcarbamoyl 4L<u dialkylcarbamoyl, in which the alkyl moiety has 1 to 4 carbon atoms, respectively 1 to 4;
Alkylthio, alkylsulfinyl, alkylsulfonyl having 4 carbon atoms, alkylcarbonyloxy having 2 to Is carbon atoms, alkylcarbonylamino or cyano group having 2 to 5 carbon atoms] sulfonamide group In the method for producing a phenoxybenzoic acid derivative or a salt thereof, [wherein X is a chlorine, bromine or iodine atom, B, C, D, E
and the acid halide having the above meaning in formula (1) is reacted with the sulfonamide of the formula % [wherein R- also has the above meaning], and this reaction is caused to react with the sulfonamide of the formula The reaction is carried out in the absence of hydrogen-acid by-products and at a temperature such that the gaseous hydrogen-acid by-product is removed from the reaction medium from the vicinity of the formation, provided that this temperature is lower than the decomposition temperature of equation (1) without formation. A method for producing a phenoxybenzoic acid derivative or a salt thereof having a characteristic sulfonamide group. (2) The method according to claim 1, wherein the reaction is carried out in the presence of an excess amount of acid halogen atoms of formula (It). (a) The method according to claim 2, wherein the molar ratio of acid halide of formula (1)/sulfonamide of formula (@) is within the range of 1.5 to 5. (4) Reaction temperature: 80-200°C, preferably 90-1
The method according to claim 2 or fga, wherein the temperature is 60°C. (5) The method according to claim 1, wherein the reaction is carried out in the presence of an excess amount of sulfonand. (6) The method according to claim 5, wherein the molar ratio of the sulfonamide of the formula (transformed)/the phantom acid halide of the formula (transformed) is within the range of 1.5 to 5. (7) The reaction temperature is set to 90°C. ~200℃, preferably 140~
The method according to claim 53, item 6, wherein the temperature is 160°C. (8) The method according to any one of claims H 1 to 7, wherein the reaction is carried out in the presence of a solvent having a boiling point higher than the reaction temperature. (9) The method according to claim 8, wherein the solvent is a hydrocarbon. 10. The method according to claim 9, wherein the (conversion) solvent is cumene and the temperature is 130 to 150C. (b) A method according to any one of claims 1 to 8, wherein the reaction is carried out in the presence of a solvent that has catalytic properties with respect to the reaction. (2) The method according to claim 11, wherein the solvent is dimethylformamide or dimethylacedobumide and the temperature is within the range of 80°C to the boiling point of the solvent. (to) Claim 11 that increases the temperature by more than 90°C
The method described in section. 04 Based on formulas (1) and (n), B and X
is a chlorine atom, A is a chlorine atom, and
14. The method according to any one of claims 1 to 13, wherein C1E and F are hydrogen atoms and D is CF3. (2) A method according to claim 6 or 7, in which a sulfonamide is used in which R1 is an alkyl or CF group, preferably a methyl group. (Claims 1 to 15 in which a compound of formula Li2 is reacted with a compound of formula C&-so, - corner)
Method described in any of the sections ◇
JP57130216A 1981-07-27 1982-07-26 Manufacture of phenoxybenzoic acid derivative containing sulfonamide group Granted JPS5826860A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28693881A 1981-07-27 1981-07-27
US286938 1981-07-27

Publications (2)

Publication Number Publication Date
JPS5826860A true JPS5826860A (en) 1983-02-17
JPH0149262B2 JPH0149262B2 (en) 1989-10-24

Family

ID=23100791

Family Applications (1)

Application Number Title Priority Date Filing Date
JP57130216A Granted JPS5826860A (en) 1981-07-27 1982-07-26 Manufacture of phenoxybenzoic acid derivative containing sulfonamide group

Country Status (23)

Country Link
JP (1) JPS5826860A (en)
KR (1) KR880002591B1 (en)
AT (1) AT385985B (en)
BE (1) BE893940A (en)
BR (1) BR8204357A (en)
CA (1) CA1194472A (en)
CH (1) CH652384A5 (en)
DD (1) DD203716A5 (en)
DE (1) DE3227847A1 (en)
DK (1) DK333282A (en)
ES (1) ES514352A0 (en)
FR (1) FR2510105A1 (en)
GB (1) GB2103611B (en)
HU (1) HU191186B (en)
IE (1) IE53978B1 (en)
IL (1) IL66197A (en)
IT (1) IT1198399B (en)
LU (1) LU84295A1 (en)
NL (1) NL8202994A (en)
PL (1) PL136683B1 (en)
PT (1) PT75322B (en)
RO (1) RO85388B (en)
SU (1) SU1215620A3 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8628109D0 (en) * 1986-11-25 1986-12-31 Ici Plc Chemical process
US11834714B2 (en) 2021-12-20 2023-12-05 Enumerix, Inc. Detection and digital quantitation of multiple targets

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2960664D1 (en) * 1978-01-19 1981-11-19 Ici Plc Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them
DE3068101D1 (en) * 1979-07-18 1984-07-12 Ici Plc Diphenyl ether compounds, and herbicidal compositions and processes utilising them

Also Published As

Publication number Publication date
DK333282A (en) 1983-01-28
IE53978B1 (en) 1989-05-10
RO85388A (en) 1984-11-25
RO85388B (en) 1984-11-30
IL66197A0 (en) 1982-11-30
DD203716A5 (en) 1983-11-02
CA1194472A (en) 1985-10-01
DE3227847A1 (en) 1983-02-10
IT8222545A0 (en) 1982-07-23
CH652384A5 (en) 1985-11-15
PT75322A (en) 1982-08-01
LU84295A1 (en) 1984-03-22
JPH0149262B2 (en) 1989-10-24
PL136683B1 (en) 1986-03-31
ES8306108A1 (en) 1983-05-01
BR8204357A (en) 1983-07-19
FR2510105A1 (en) 1983-01-28
IT8222545A1 (en) 1984-01-23
IT1198399B (en) 1988-12-21
GB2103611B (en) 1985-04-03
AT385985B (en) 1988-06-10
IL66197A (en) 1985-11-29
NL8202994A (en) 1983-02-16
ATA290082A (en) 1987-11-15
FR2510105B1 (en) 1984-09-07
GB2103611A (en) 1983-02-23
IE821786L (en) 1983-01-27
KR880002591B1 (en) 1988-12-03
HU191186B (en) 1987-01-28
BE893940A (en) 1983-01-26
ES514352A0 (en) 1983-05-01
KR840000466A (en) 1984-02-22
PL237639A1 (en) 1983-05-23
PT75322B (en) 1985-11-29
SU1215620A3 (en) 1986-02-28

Similar Documents

Publication Publication Date Title
JP3703869B2 (en) Process for producing hydroxyphenyl-1,3,5-triazine
JPH021470A (en) Sulfonium compound and production thereof
JPS5826860A (en) Manufacture of phenoxybenzoic acid derivative containing sulfonamide group
JP2007238472A (en) Monoglycidylisocyanuric acid compound
JPH0390057A (en) Chlorofluorobenzonitrile and production thereof
JP2000109314A (en) Production of alkali metallic cyanate and cyanuric acid derivative
GB2327419A (en) Improved synthesis of 1,3-benzoxazin-4-ones
JP5342217B2 (en) Method for producing organophosphorus compound
US5908955A (en) Process for producing alkyl 3-amino-4-substituted benzoates
PL69905B1 (en)
CA1215357A (en) Process for the preparation of aryloxybenzoic acids containing a sulphonamide group
HU213629B (en) Process for the preparation of acid chloride compounds
JPS6072847A (en) Manufacture of alpha-chloroformate chrolide
JPH0273044A (en) Difluoroanthranilic acid and preparation thereof
KR840001563B1 (en) Process for preparing 1-carbymayl-3-(3,5-dichlorophenyl)-hydantoins
JP4336501B2 (en) Novel 4,4 &#34;-dialkoxyterphenyls
JP3653779B2 (en) Process for producing 1,2,3-trichloro-4,6-dinitrobenzene
JPH01117849A (en) Production of 2,6-dihaloaniline derivative
JPH0421646A (en) Preparation of chloroethyl ether
JPS59118761A (en) Manufacture of aryloxybenzoic acid containing sulfonamide group
JPS62145047A (en) Production of dinitrophenyl ethers
JPS5837314B2 (en) benzotriazole
JP2005082569A (en) NEW 4,4&#39;&#39;-DIALKOXY-p-TERPHENYLS
JPS5888372A (en) Manufacture of n-carbamoylbenzoic acid sulfimide derivative
JPH0592942A (en) Method for alkylating aromatic amine