JPH0149262B2 - - Google Patents

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Publication number
JPH0149262B2
JPH0149262B2 JP57130216A JP13021682A JPH0149262B2 JP H0149262 B2 JPH0149262 B2 JP H0149262B2 JP 57130216 A JP57130216 A JP 57130216A JP 13021682 A JP13021682 A JP 13021682A JP H0149262 B2 JPH0149262 B2 JP H0149262B2
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.)
Expired
Application number
JP57130216A
Other languages
Japanese (ja)
Other versions
JPS5826860A (en
Inventor
Ai Heiba Eruuamadei
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

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Classifications

    • 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
    • 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
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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
    • C07C323/39—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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    • 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
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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
    • 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
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    • 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
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    • 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
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    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
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    • 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
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    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
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    • C07C63/06—Benzoic acid
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    • 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
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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
    • 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
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    • 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
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    • 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
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    • 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

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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は、除草性を有するスルホンアミド基を
含んだ或る種のフエノキシ安息香酸誘導体の改良
製造方法に関するものである。 スルホンアミド基を有するフエノキシ安息香酸
の除草性誘導体は、ヨーロツパ特許出願第3416号
および23392号各明細書から公知である。 これらの特許出願明細書は、式 〔上記式中Ａは水素、弗素、塩素、臭素、沃素、
ニトロ基、−Ｎ＝NCF3、PO3H2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、
NH2、NHOH、N2 +、カルボキシル基もしくは
その官能性誘導基の１種、モノアルキルアミノも
しくはジアルキルアミノ基、基NH−CO−R1（こ
こで、R1はアルキル、アルコキシ、モノアルキ
ルアミノまたはジアルキルアミノ基である）、ア
ルキル基、トリアルキルアンモニオ、NHSO2R2
（ここで、R2はアルキルまたはフエニル基であ
る）、NHCONHSO2R2（ここで、R2は上記の意味
を有する）、アルキルチオ、アルキルスルフイニ
ル、アルキルスルホニル、ジアルキルスルホニ
オ、ジアノスルホニル、ヒドロキシ、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
置換されたアルコキシ、SH、ニトロソ、−SCN、
アジド、CF3、 The present invention relates to an improved method for producing certain phenoxybenzoic acid derivatives containing sulfonamide groups having herbicidal properties. Herbicidal derivatives of phenoxybenzoic acid having sulfonamide groups are known from European Patent Applications Nos. 3416 and 23392. These patent application specifications are based on the formula [In the above formula, A is hydrogen, fluorine, chlorine, bromine, iodine,
nitro group , -N= NCF3 , PO3H2 and its alkyl ester group having 1 to 4 carbon atoms,
NH 2 , NHOH, N 2 + , carboxyl group or one of its functional derivatives, monoalkylamino or dialkylamino group, group NH-CO-R 1 (where R 1 is alkyl, alkoxy, monoalkylamino) or dialkylamino group), alkyl group, trialkylammonio, NHSO 2 R 2
(where R 2 is an alkyl or phenyl group), NHCONHSO 2 R 2 (where R 2 has the above meaning), alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonio, dianosulfonyl , hydroxy, alkanoyloxy, alkoxy, alkoxy substituted with alkoxycarbonyl, SH, nitroso, -SCN,
Azide, CF 3 ,

〔式中、X3は上記の意味を有する〕[In the formula, X 3 has the above meaning]

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−ジメチルアニ
リンもしくはピリジンのような第３級アミン、た
とえば無水炭酸カリウムのようなアルカリ金属炭
酸塩、またはたとえば弗化セシウムのようなアル
カリ金属弗化物の存在下で反応させることにより
製造することができる。 R4が水素原子である式（）の化合物は、公
知方法によりたとえば１〜４個の炭素原子を有す
るジアゾアルカンとの反応によりアルキル化し
て、R4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。 式（）の化合物と式（）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、ヨーロツパ
特許出願第23392号の実施例14については収率が
27％であり、また実施例34については収率9.5％
と算定できる）。ジアシル化反応の促進により収
率が低下するのであるが、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。 本発明の一目的は、これらの欠点を克服するこ
とである。 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、HI）が生成されるそばから気体として反
応媒体より除去されるような温度、しかも式
（）の反応生成物の“認めうる分解”を伴なわ
ないように温度にて、式（）のスルホンアミド
と反応させることを特徴とする。 本発明の方法によれば、フエノキシ安息香酸の
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％しばしば
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は、公知方法の場
合よりもずつと簡単である。 実際上、本発明に使用する酸ハロゲン化物は式
（）の酸ハロゲン化物である。Ａが基NO2また
は弗素、塩素、臭素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
子でありかつＤが基CF3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、R3
がアルキル基、特にCH3または基CF3であるよう
な式（）のスルホンアミドを使用するのも好適
である。 本発明の方法を行ないうる温度は、特に式
（）の酸ハロゲン化物または式（）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。 たとえば、酸ハロゲン化物（）が大過剰に存
在する場合、すなわち（）／（）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（）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90〜160℃の範囲である。 未反応のハロゲン化物（）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、トルエンもしく
はキシレン、ハロゲン化炭化水素、特にクロルベ
ンゼン、CS2、テトラヒドロフラン、ジオキサン
などで洗浄することにより反応媒体から回収する
ことができる。 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（）／（）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140〜160℃である。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
させるのに充分な温度でなければならない。過剰
のスルホンアミド（）は、これを水またはこの
反応体（）に対して不活性の他の溶剤により洗
浄して反応媒体から回収することができる。 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。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
（）とスルホンアミド（）との反応によりフ
エノキシベンゾイルスルホンアミド（）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。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164℃で沸とう
する）が特に有利であり、それらの使用により、
反応と比較的低い温度、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
沸点より僅かに低い温度において実施できるよう
になり、かつ、反応速度はより高速となる。 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、本発明の
範囲はこれにより限定されるものでない。 実施例 １ メタンスルホンアミド（2g、0.021モル）を５
−〔2′−クロル−4′（トリフルオロメチル）−フエ
ノキシ〕−２−ニトロ−ベンゾイルクロライド
（3.8g、0.01モル）と混合した。この混合物を150
℃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。この溶液を過しそして液を
希塩酸で酸性化させ、これにより式（）の生成
物を沈澱させた。かくして、収率71％をもつて、
195〜197℃にて溶融しかつ1692cm-1（Ｃ＝Ｏ基）
に赤外吸収帯を有する生成物（3.1g）が得られ
た。この生成物は式 を有する。 実施例 ２ 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を使用し
た。反応生成物は、混合物を冷却した後にイソプ
ロパノールからの再結晶により直接に単離した。
これにより、式（）の生成物が収率64％
（185g）で得られた。この生成物の構造は、赤外
吸収スペクトル（1692cm-1における吸収帯）およ
び核磁気共鳴スペクトル（3.5ppmにてシングレ
ツト、8.07ppmにてマルチブレツト）により確認
された。 比較のために、ヨーロツパ特許出願第23392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つた場合、収率は僅
か25％であつた。 of a sulfonamide at a temperature of 25 to 140° C. in the presence of an acid acceptor, especially a tertiary amine such as N,N-dimethylaniline or pyridine, an alkali metal carbonate such as anhydrous potassium carbonate, or For example, it can be produced by reacting in the presence of an alkali metal fluoride such as cesium fluoride. Compounds of formula () in which R 4 is a hydrogen atom can be alkylated by known methods, for example by reaction with a diazoalkane having 1 to 4 carbon atoms, so that R 4 is an alkyl group having 1 to 4 carbon atoms. Corresponding compounds that are radicals can be generated. This method for the condensation of compounds of formula () with compounds of formula () has a number of drawbacks. For example, the yield is unfavorable (e.g. for example 14 of European Patent Application No. 23392, the yield is
27% and 9.5% yield for Example 34
). The yield decreases due to promotion of the diacylation reaction, and the main reason for this is thought to be the presence of acid acceptors. Furthermore, the use of acid acceptors makes isolation and purification of the final product more difficult and more expensive. One aim of the invention is to overcome these drawbacks. The process according to the invention comprises converting an acid halide (preferably chloride, bromide or iodide) in the absence of an acid acceptor and using hydrohalic acid (HCl,
(HBr, HI) is removed from the reaction medium as a gas from the vicinity of its formation, and at such a temperature that there is no appreciable decomposition of the reaction product of formula (). Characterized by reaction with sulfonamide. 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%, often at least about 50%, and of the final product. Recovery and purification operations are much simpler than with known methods. In practice, the acid halide used in the present invention is an acid halide of formula (). A is the group NO 2 or a fluorine, chlorine, bromine or iodine atom, and B
It is preferred to use halides of the formula in which is a halogen atom, C, E and F are hydrogen atoms and D is a radical CF 3 . Furthermore, R 3
It is also suitable to use sulfonamides of the formula () in which is an alkyl group, in particular a CH 3 or a group CF 3 . The temperature at which the process of the invention can be carried out depends, in particular, on whether either the acid halide of the formula () or the sulfonamide of the formula () is present in large excess or whether a solvent with catalytic properties is used or not. It will vary depending on the situation. For example, when the acid halide () is present in large excess, i.e., when the molar ratio ()/() is in the range of about 1.5 to 5, the acid halide () can serve as a solvent for the reaction. The reaction temperature can be set at 80 to 200℃, but
Preferably it is in the range of 90 to 160°C. The unreacted halide () can be washed with an inert solvent such as a hydrocarbon, especially pentane, hexane, heptane, cyclopentane, cyclohexane, cycloheptane, benzene, toluene or xylene, a halogenated hydrocarbon, especially chlorobenzene, CS 2 , tetrahydrofuran, dioxane, etc., from the reaction medium. When an excess amount of sulfonamide is used, i.e. when the compound ()/() molar ratio is in the range 1.5-5, the reaction temperature is generally 90-200°C,
Preferably it is 140-160°C. In either case, the reaction temperature must be at least sufficient to melt the reaction medium. Excess sulfonamide () can be recovered from the reaction medium by washing it with water or other solvents inert towards the reactant (). 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 up to Advantageously, the 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. 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, a catalytic solvent is used for the reaction of acid halide () with sulfonamide () to form phenoxybenzoyl sulfonamide (). In this respect, dimethylformamide (=DMF,
Particularly advantageous are dimethylacetamide (=DMAC, which boils at about 164°C); their use
This allows the reaction to be carried out at relatively low temperatures, such as from 80 to 120°C, preferably from 90 to 110°C, or slightly below the boiling point of these solvents, and the reaction rate is faster. EXAMPLES Hereinafter, the present invention will be explained with reference to examples and how it can be practiced will be specifically shown, but the scope of the present invention is not limited thereby. Example 1 Methanesulfonamide (2 g, 0.021 mol) was added to 5
-[2'-chloro-4'(trifluoromethyl)-phenoxy]-2-nitro-benzoyl chloride (3.8 g, 0.01 mole). 150% of this mixture
Heated at ℃ 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 liquor acidified with dilute hydrochloric acid, thereby precipitating the product of formula (). Thus, with a yield of 71%,
Melts at 195-197℃ and 1692cm -1 (C=O group)
A product (3.1 g) having an infrared absorption band was obtained. This product has the formula has. Example 2 Example 1 was repeated, but this time using 250 g of acid chloride and 130 g of methanesulfonamide. The reaction product was isolated directly by recrystallization from isopropanol after cooling the mixture.
This gives the product of formula () in 64% yield
(185g) was obtained. The structure of the product was confirmed by infrared absorption spectra (absorption band at 1692 cm -1 ) and nuclear magnetic resonance spectra (singlet at 3.5 ppm, multiplet at 8.07 ppm). For comparison, when the reaction was carried out using the method described in the Examples of European Patent Application No. 23392 and using pyridine as the acid acceptor, the yield was only 25%.

Claims (1)

【特許請求の範囲】 １ 式 〔式中、Ａは水素、弗素、塩素、臭素、沃素、ニ
トロ基、−Ｎ＝NCF3、PO3H2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、
NH2、NHOH、N2 +、カルボキシル基もしくは
その官能性誘導基の１種、モノアルキルアミノも
しくはジアルキルアミノ基、基NH−CO−R1（こ
こで、R1はアルキル、アルコキシ、モノアルキ
ルアミノまたはジアルキルアミノ基である）、ア
ルキル基、トリアルキルアンモニオ、NHSO2R2
（ここで、R2はアルキルまたはフエニル基であ
る）、NHCONHSO2R2（ここで、R2は上記の意味
を有する）、アルキルチオ、アルキルスルフイニ
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、−
SCN、アジド、CF3、【式】 またアシルであり、 Ｂは水素、弗素、塩素、臭素、沃素、アルキ
ル、アルコキシ、アルキルスルフイニルもしくは
アルキルスルホニル基、CF3、NO2、CN、NH2、
NHCOR1（ここで、R1は上記に定義した通りであ
る）またはCONH2であり、 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CF3、アル
キルチオ、アルキルスルフイニル、アルキルスル
ホニル、ハロゲノアルキル、スルフアモイル、ホ
ルミル、アルキルカルボニル、CNまたはジメチ
ルアミノ基であり、 Ｅは水素、ハロゲノアルキル、アルコキシ、ア
ルキルスルフイニルまたはアルキルスルホニル
基、CN、CF3、NH2、CONH2またはNH−CO
−R1（ここで、R1は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（R4）SO2R3であり、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
ル基であり、 R3はフエニル、ピリジルまたはチエニル基
（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
より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は
ジ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、アルキルスルフイ
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エノキシ安息香酸
誘導体またはその塩を製造する方法において、 式 〔式中、Ｘは塩素、臭素もしくは沃素原子であ
り、Ａ、Ｂ、Ｃ、Ｄ、ＥおよびＦは式（）にお
いて上記した意味を有する〕 の酸ハロゲン化物を式 R3SO2NH2 （） 〔式中、R3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り除去されるような温度に
て行ない、ただしこの温度は式（）の生成物の
分解温度より低いことを特徴とするスルホンアミ
ド基を有するフエ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（）の酸ハロゲン化物の
存在下で行なう特許請求の範囲第１項記載の方
法。 ３ 式（）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 反応温度を80〜200℃、好ましくは90〜160℃
とする特許請求の範囲第２項または第３項記載の
方法。 ５ 反応を過剰量のスルホンアミドの存在下で行
なう特許請求の範囲第１項記載の方法。 ６ 式（）のスルホンアミド／式（）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５項または第６項記載
の方法。 ８ 反応を、反応温度より高い沸点を有する溶剤
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。 １０ 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。 １１ 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。 １２ 溶剤をジメチルホルムアミドもしくはジメ
チルアセトア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。 １３ 温度を90℃より高くする特許請求の範囲第
１２項記載の方法。 １４ 式（）および（）において、Ｂおよび
Ｘが塩素原子であり、Ａが塩素原子またはNO2
であり、Ｃ、ＥおよびＦが水素原子でありかつ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。 １５ R3がアルキルまたはCF3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。 １６ 式 の化合物を式 CH3−SO2−NH2 の化合物と反応させる特許請求の範囲第１項乃至
第１５項のいずれかに記載の方法。[Claims] 1 formula [wherein A is hydrogen, fluorine, chlorine, bromine, iodine, nitro group, -N= NCF3 , PO3H2 and its alkyl ester group having 1 to 4 carbon atoms,
NH 2 , NHOH, N 2 + , carboxyl group or one of its functional derivatives, monoalkylamino or dialkylamino group, group NH-CO-R 1 (where R 1 is alkyl, alkoxy, monoalkylamino) or dialkylamino group), alkyl group, trialkylammonio, NHSO 2 R 2
(wherein R2 is an alkyl or phenyl group), NHCONHSO2R2 (wherein R2 has the above meaning), alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylsulfonio, cyanosulfonyl , Hydroxyl, alkanoyloxy, alkoxy, alkoxy substituted with alkoxycarbonyl, SH, nitroso, -
SCN, azide, CF 3 , [Formula] is also acyl, B is hydrogen, fluorine, chlorine, bromine, iodine, alkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CF 3 , NO 2 , CN, NH 2 ,
NHCOR 1 (where R 1 is as defined above) or CONH 2 , C is hydrogen, halogen or an alkyl or dialkylamino group, D is fluorine, chlorine, bromine, iodine or CF 3 , Alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, sulfamoyl, formyl, alkylcarbonyl, CN or dimethylamino group, E is hydrogen, halogenoalkyl, alkoxy, alkylsulfinyl or alkylsulfonyl group, CN, CF3 , NH 2 , CONH 2 or NH−CO
-R 1 , where R 1 has the meaning given above, F has one of the meanings indicated for B, and R is the group -CON(R 4 )SO 2 R 3 , where and R 4 is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R 3 is a phenyl, pyridyl or thienyl group (these groups optionally contain 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 substituted with one or more fluorine , chlorine, bromine or iodine atoms, preferably CF3 , or by one or more of the following substituents: carboxyl, having 2 to 5 carbon atoms alkoxycarbonyl, alkylcarbonyl having 2 to 5 carbon atoms, monoalkylcarbamoyl or dialkylcarbamoyl having 1 to 4 carbon atoms in the alkyl moiety, alkylthio, alkylsulfinyl each having 1 to 4 carbon atoms , alkylsulfonyl, alkylcarbonyloxy having 2 to 5 carbon atoms, alkylcarbonylamino or cyano group having 2 to 5 carbon atoms] A method for producing a phenoxybenzoic acid derivative having a sulfonamide group or a salt thereof In the formula [In the formula, X is a chlorine, bromine or iodine atom, and A, B, C, D, E and F have the above meanings in the formula ()] An acid halide of the formula R 3 SO 2 NH 2 ( ) in which R 3 also has the abovementioned meanings, and the reaction is carried out in the absence of an acid acceptor and the gaseous hydrogen acid by-product is removed from the reaction medium from the point where it is produced. A method for producing a phenoxybenzoic acid derivative having a sulfonamide group or a salt thereof, characterized in that the temperature is lower than the decomposition temperature of the product of formula (). 2. The method according to claim 1, wherein the reaction is carried out in the presence of an excess amount of an acid halide of formula (). 3. The method according to claim 2, wherein the molar ratio of acid halide of formula ()/sulfonamide of formula () is within the range of 1.5 to 5. 4. Reaction temperature: 80-200℃, preferably 90-160℃
The method according to claim 2 or 3. 5. The method according to claim 1, wherein the reaction is carried out in the presence of an excess amount of sulfonamide. 6. The method according to claim 5, wherein the molar ratio of sulfonamide of formula ()/acid halide of formula () is within the range of 1.5 to 5. 7. Reaction temperature 90~200℃, preferably 140~160℃
7. The method according to claim 5 or 6, wherein the temperature is .degree. 8 Claims 1 to 7 in which the reaction is carried out in the presence of a solvent having a boiling point higher than the reaction temperature
The method described in any of the paragraphs. 9. The method according to claim 8, wherein the solvent is a hydrocarbon. 10. The method according to claim 9, wherein the solvent is cumene and the temperature is 130-150°C. 11. A process 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 for this reaction. 12. The method according to claim 11, wherein the solvent is dimethylformamide or dimethylacetamide and the temperature is within the range of 80°C to the boiling point of the solvent. 13. The method according to claim 12, wherein the temperature is higher than 90°C. 14 In formulas () and (), B and X are chlorine atoms, and A is a chlorine atom or NO 2
, C, E and F are hydrogen atoms, and D
14. The method according to any one of claims 1 to 13, wherein is CF3 . 8. Process according to claim 6 or 7, characterized in that sulfonamides are used in which 15 R 3 is an alkyl or CF 3 group, preferably a methyl group. 16 formula A method according to any of claims 1 to 15, wherein a compound of the formula CH3 - SO2 - NH2 is reacted with a compound of the formula CH3-SO2-NH2.
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)

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

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AT (1) AT385985B (en)
BE (1) BE893940A (en)
BR (1) BR8204357A (en)
CA (1) CA1194472A (en)
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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)
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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
PL136683B1 (en) 1986-03-31
JPS5826860A (en) 1983-02-17
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

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