GB653027A - Manufacture of insect-repelling amides of chlorobenzoic acid and compositions prepared therefrom - Google Patents
Manufacture of insect-repelling amides of chlorobenzoic acid and compositions prepared therefromInfo
- Publication number
- GB653027A GB653027A GB1521948A GB1521948A GB653027A GB 653027 A GB653027 A GB 653027A GB 1521948 A GB1521948 A GB 1521948A GB 1521948 A GB1521948 A GB 1521948A GB 653027 A GB653027 A GB 653027A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- ethyl
- acid
- chloride
- chlorobenzamides
- 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
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Abstract
Chlorobenzamides of formula <FORM:0653027/IV (b)/1> where R is ethyl or allyl and X is hydrogen or chlorine are prepared by (1) reacting a compound <FORM:0653027/IV (b)/2> with a compound Y1NR2, where Y=OH and Y1=H; Y=Cl or OAcyl and Y1=H; Y=Cl and Y1=Na; Y=Cl and Y1=HCl.H; Y= OMe and Y1=H; Y=NH2 and Y1=H; Y= ONa and Y1=ClCO-; or Y=ONa and Y1= Aryl SO2-, e.g. p-MeC6H4SO2-; (2) reducing the nitro group of the corresponding o-nitrobenzamide (which may be prepared from the corresponding o-nitrobenzoic acid chloride and the amine NHR2) to an amino group, diazotizing and converting by the Sandmeyer method to a chloro group; and (3) alkylating the compound <FORM:0653027/IV (b)/3> where Z is hydrogen, ethyl or allyl, to introduce an ethyl or allyl group. In the examples, 2-chlorobenzoyldiethylamide is prepared by the reaction of diethylamine with (1) and (2) o-chlorobenzoyl chloride (prepared by chlorination of o-chlorobenzaldehyde with chlorine or thionyl chloride) or (3) methyl o-chlorobenzoate; by the reaction of (4) sodium 2-chlorobenzoate with diethylcarbamyl chloride; (5) o-chlorobenzoic acid with p-toluene-N-diethylsulphonamide; it is also prepared (6) from 2-nitrobenzoyldiethylamide (prepared from 2-nitrobenzoyl chloride and diethylamine) by reduction of the nitro group, diazotization, and reaction with aqueous cuprous chloride.ALSO:Chlorobenzamides of the formula. <FORM:0653027/VI/1> where X is hydrogen or chlorine and R is ethyl or allkyl are used as the active ingredient in insect-repelling compositions. They may be admixed with powders such as calcium phosphate or carbonate, kaolin, magnesia, boric acid, cork or wood meal, talc, and starch powder; alternatively they may be used as solutions in alcohols, e.g. ethanol, propanols, benzyl alcohol, glycerol and cyclohexanol esters, e.g. ethyl acetate, ethers, e.g. glycol monoethyl ether, ketones, e.g. propanone and butanone 2 and cyclohexanone, oils such as olive, arachis, castor and paraffin oils, kerosenes and alkyl and hydrogenated naphthalenes. The benzamides may be emulsified in water with emulsifiers and wetting agents, or blended into ointments with walrus fat, wool grease, fatty alcohols, petroleum jelly, lipoids, stearins, fatty acid salts, thiethanolamine, fatty alcohol sulphonates, cellulose ethers, vegetable mucilages, aluminium hydroxide gel, silica gel, zinc and titamium oxides, with solvents if desired. The benzamides in solution or emulisified may be used to impregnate textiles. The benzamides may be dissolved in liquids such as dichlorodifluoromethane to produce aerosol sprays, or mixed with charcoal, cellulose and potassium nitrate for a fumigation composition. Other substances which may be included in these benzamide compositions are phthalate esters, 2-ethylhexanediol-1: 3 x: x-dimethyl-x 1-carbobutoxydihydropyran, crotonic acid N-ethyl-o-toluidide, menthyl salicylate or anthranilate, phenyl salicylate, quinine salts, umbelliferone, aesculin, naphtholsulphonic acid salts, soluble calcium, magnesium and strontium salts, perfumes, and anti-oxidants. In the examples, chlorobenzamides (e.g. o-chlorobenzoyl-N-diethylamide) is compounded with (1) talc, (2) castor oil and isopropanol, (3) water using a fatty acid sulphonate, (4) paraffin oil, stearic acid, wool grease, wax, glycerol, triethanolamine, water, and ammonia.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1521948A GB653027A (en) | 1948-06-05 | 1948-06-05 | Manufacture of insect-repelling amides of chlorobenzoic acid and compositions prepared therefrom |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1521948A GB653027A (en) | 1948-06-05 | 1948-06-05 | Manufacture of insect-repelling amides of chlorobenzoic acid and compositions prepared therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
GB653027A true GB653027A (en) | 1951-05-09 |
Family
ID=10055149
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1521948A Expired GB653027A (en) | 1948-06-05 | 1948-06-05 | Manufacture of insect-repelling amides of chlorobenzoic acid and compositions prepared therefrom |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB653027A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3161564A (en) * | 1960-10-03 | 1964-12-15 | Salsbury S Lab Dr | Veterinary composition containing halo-nitro-benzamides and methods of using same |
US3620818A (en) * | 1968-10-09 | 1971-11-16 | Monsanto Co | Method of imparting flame resistant properties to nylon and the treated product |
US4273674A (en) * | 1978-01-13 | 1981-06-16 | General Electric Company | Thermal detecting paint compositions |
EP0036135A2 (en) * | 1980-03-13 | 1981-09-23 | Henkel Kommanditgesellschaft auf Aktien | Deodorant cosmetic compositions |
US7867479B2 (en) * | 2003-11-14 | 2011-01-11 | Bug Buster, Ltd. | Compounds to affect insect behavior and/or bird behavior |
-
1948
- 1948-06-05 GB GB1521948A patent/GB653027A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3161564A (en) * | 1960-10-03 | 1964-12-15 | Salsbury S Lab Dr | Veterinary composition containing halo-nitro-benzamides and methods of using same |
US3620818A (en) * | 1968-10-09 | 1971-11-16 | Monsanto Co | Method of imparting flame resistant properties to nylon and the treated product |
US4273674A (en) * | 1978-01-13 | 1981-06-16 | General Electric Company | Thermal detecting paint compositions |
EP0036135A2 (en) * | 1980-03-13 | 1981-09-23 | Henkel Kommanditgesellschaft auf Aktien | Deodorant cosmetic compositions |
EP0036135A3 (en) * | 1980-03-13 | 1982-03-31 | Henkel Kommanditgesellschaft auf Aktien | Deodorant cosmetic compositions |
US4425327A (en) | 1980-03-13 | 1984-01-10 | Henkel Kommanditgesellschaft Auf Aktien | Method of suppressing body odor with aminobenzoic acid amides |
US7867479B2 (en) * | 2003-11-14 | 2011-01-11 | Bug Buster, Ltd. | Compounds to affect insect behavior and/or bird behavior |
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