GB753766A - Improvements in or relating to carbamic acid esters - Google Patents

Improvements in or relating to carbamic acid esters

Info

Publication number
GB753766A
GB753766A GB13278/54A GB1327854A GB753766A GB 753766 A GB753766 A GB 753766A GB 13278/54 A GB13278/54 A GB 13278/54A GB 1327854 A GB1327854 A GB 1327854A GB 753766 A GB753766 A GB 753766A
Authority
GB
United Kingdom
Prior art keywords
chlorophenyl
aqueous
dichlorophenyl
general formula
formula
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
GB13278/54A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc 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 SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB753766A publication Critical patent/GB753766A/en
Expired legal-status Critical Current

Links

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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises carbamic acid esters conforming to the general formula <FORM:0753766/IV(a)/1> in which R1 and R2 are the same or different each representing an alkyl group containing not more than six carbon atoms and Ar represents a phenyl radical substituted by at least one chlorine or bromine atom. The carbamic esters of the above general formula are prepared by a process which comprises (a) reacting a substituted carbamyl chloride of the general formula <FORM:0753766/IV(a)/2> with a sodium salt of a phenol of the formula Ar OH, or (b) reacting a compound of the formula ArOCOOAr with an amine of the formula NHR1(R2), the symbols R1, R2 and A having the significance set forth above. Specific products mentioned include p-chlorophenyl-, 2:4-dichlorophenyl-, 3:4-dichlorophenyl-, 2-methyl-4-chloropdenyl and 2:4:5-trichlorophenyl dimethylcarbamates, p-chlorophenyl diethylcarbamate and p-chlorophenyl dibutylcarbamate. In examples: 2:4-dichlorophenyl dimethyl carbamate is obtained by treating a mixture of 2:4-dichlorophenol and aqueous caustic soda with dimethylcarbamyl chloride, extracting the product with toluene and fractionating the extract (I); p-chlorophenyl carbonate, obtained by treating p-chlorophenol with aqueous caustic soda solution and phosgene, is heated with aqueous dimethylamine and the organic layer which forms is separated, combined with a benzene extract obtained from the acidified aqueous layer and fractionated to obtain p-chlorophenyl dimethylcarbamate (II). The corresponding brominesubstituted products may be obtained by corresponding procedures using bromophenols in place of the chlorophenols. The products of the invention may be employed in insecticidal compositions and in addition to diluents may be mixed with 0 : 0-diethyl 0-p-nitrophenyl thiophosphate (see Group VI).ALSO:An insecticidal composition comprises a carbamic acid ester conforming to the general formula: <FORM:0753766/VI/1> in which R1 and R2 are the same or different, each representing an alkyl group containing not more than six carbon atoms and Ar represents a phenyl radical substituted by at least one chlorine or bromine atome (see Group IV(b)) and a solid or liquid diluent. Specific carbamtes mentioned include p-chlorophenyl-, 2 : 4-dichlorophenyl-, 3 : 4-dichlorophenyl-, 2-methyl-4-chlorophenyl and 2: 4 : 5-trichlorophenyl dimethylcarbamates, p-chlorophenyl diethyl carbamate and p-chlorophenyl dibutylcarbamate. The compositions may comprise additional insecticidal or fungicidal agents e.g. O : O-diethyl O - p - nitrophenyl thio-phosphate. Diluents mentioned include powders such as talc and kaolin, and dispersing or wetting agents may be employed to produce wettable powders capable of forming pastes, solutions or emulsions in aqueous or organic media. For the preparation of aqueous dispersions solvents, emulsifiers and adhesives may be used and for the preparation of aerosols and spraying solutions volatile solvents may be employed. Aqueous p suspensions of several of the carbamates are referred to.
GB13278/54A 1953-05-16 1954-05-06 Improvements in or relating to carbamic acid esters Expired GB753766A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1081976T 1953-05-16

Publications (1)

Publication Number Publication Date
GB753766A true GB753766A (en) 1956-08-01

Family

ID=9610443

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13278/54A Expired GB753766A (en) 1953-05-16 1954-05-06 Improvements in or relating to carbamic acid esters

Country Status (3)

Country Link
CH (1) CH320209A (en)
FR (1) FR1081976A (en)
GB (1) GB753766A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3076741A (en) * 1960-06-20 1963-02-05 California Research Corp 3-sec. butyl-6-chlorophenyl n-methylcarbamate and use thereof as a pesticide
US3120557A (en) * 1962-05-18 1964-02-04 Monsanto Chemicals Pentahalophenyl carbonates
US3131215A (en) * 1960-10-06 1964-04-28 Upjohn Co 2-halo-and 2, 4-dihalo-alkylphenyl carbamates
US3402245A (en) * 1960-10-06 1968-09-17 Upjohn Co Insecticidal 2-halo- and 2, 4-dihaloalkylphenyl carbamate compositions and method for controlling insects
JPS516131B1 (en) * 1964-12-28 1976-02-25

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL81357C (en) * 1953-06-09
DE1037753B (en) * 1956-07-13 1958-08-28 Rohm & Haas Pest repellants
US2933383A (en) * 1956-11-23 1960-04-19 Union Carbide Corp Method of combating weeds using nu-substituted carbamates of 2, 4, 5-trichloro, 6-nitro phenol
US3098001A (en) * 1959-12-28 1963-07-16 Schering Ag Acaricide agent

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3076741A (en) * 1960-06-20 1963-02-05 California Research Corp 3-sec. butyl-6-chlorophenyl n-methylcarbamate and use thereof as a pesticide
US3131215A (en) * 1960-10-06 1964-04-28 Upjohn Co 2-halo-and 2, 4-dihalo-alkylphenyl carbamates
US3402245A (en) * 1960-10-06 1968-09-17 Upjohn Co Insecticidal 2-halo- and 2, 4-dihaloalkylphenyl carbamate compositions and method for controlling insects
US3120557A (en) * 1962-05-18 1964-02-04 Monsanto Chemicals Pentahalophenyl carbonates
JPS516131B1 (en) * 1964-12-28 1976-02-25

Also Published As

Publication number Publication date
CH320209A (en) 1957-03-31
FR1081976A (en) 1954-12-24

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