Patent GB-999876-A (GB)
Title: Improvements in or relating to pesticides
Inventor: PIANKA MAX
IPC: A01N37/00
Filed: 1961-05-05
Abstract: The invention relates to esters of the formula RO.CO.R1 or RO.CO.R11.CO.OR, where R is a 2,4-dinitro-6-tert.-butyl-phenyl group or a 2,4-dinitro-6-sec.-amylphenyl group, R1 is an aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic group and R11 is a divalent hydrocarbon group or a simple linkage. The radical R1 may be a saturated or a ,b -unsaturated aliphatic group which may be substituted by halogen atoms or by nitro, amino, substituted amino, salted amino, hydroxyl, carboxy, carbalkoxy, alkoxy, alkylthio, xanthyl or heterocyclic groups. More specifically R1 may be an alkyl group of 1-12 carbon atoms or an a - or b -methylvinyl group, a b ,b -dimethyl vinyl group, a b -methoxycarbonylvinyl group or a pentadien-1,3-yl group.  Alternatively, R1 may be a phenyl, chlorophenyl, naphthyl, benzyl, furyl or a -bromofuryl group.  The esters may be prepared by condensing 2,4-dinitro-6-tert.-butylphenol or 2,4-dinitro-6-sec.-amylphenol, or the corresponding phenolate, with an acid halide or acid anhydride, suitable reaction conditions being indicated in each case.  Examples are given of the manufacture of the 2,4-dinitro-6-tert.-butylphenyl esters of the following acids:-acetic, propionic, crotonic, hexoic, acrylic, sorbic, isobutyric, chloracetic, isovaleric, trimethylacetic, butyric, octoic, nonylic, lauric, methacrylic, fumaric semi-methyl ester, b -dimethylacrylic, phenylacetic, chloropropionic, benzoic, p-chlorobenzoic, p-nitrobenzoic, cyclohexane carboxylic, furoic, a -bromofuroic, oxalic, adipic, phthalic and terephthalic acids. Examples are given also of the manufacture of the 2,4-dinitro-6-sec.-amylphenyl esters of the following acids:-crotonic, acetic, isobutyric, sor bic, a -furoic, benzoic, n-butyric, propionic, acrylic, fumaric semi-methyl ester, dimethylacrylic, 1,3-hexadienic, chloracetic, phenylacetic, chloropropionic, p-chlorobenzoic, oxalic, adipic and phthalic acids. A further example describes the manufacture of 2,4-dinitro-6-tert.-butylphenyl a -(ethylxanthyl)acetate of the formula  <FORM:0999876/C2/1> The products are useful as pesticides (see Division A5).ALSO:As pesticides, use is made of esters of the formula RO.CO.R1 or RO.CO.R11.CO.OR, where R is a 2,4-dinitro-6-tert.-butyl phenyl group or a 2,4-dinitro-6-sec.-amylphenyl group, R1 is an aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic group and R11 is a divalent hydrocarbon group or a simple linkage. The radical R1 may be a saturated or a ,b -unsaturated aliphatic group which may be substituted by halogen atoms or by nitro, amino, substituted amino, salted amino, hydroxyl, carboxy, carbalkoxy, alkoxy, alkylthio, xanthyl or heterocyclic groups. More specifically R1 may be an alkyl group of 1-12 carbon atoms or an a - or b -methylvinyl group, a b -b -dimethyl vinyl group, a b -methoxycarbonylvinyl group or a pentadien-1,3-yl group.  Alternatively, R1 may be a phenyl, chlorophenyl, naphthyl, benzyl, furyl or a -bromofuryl group (see Division C2). Examples are given of the manufacture of the 2,4-dinitro-6-tert.-butylphenyl esters of the following acids: acetic, propionic, crotonic, hexoic, acrylic, sorbic, isobutyric, chloracetic, isovaleric, trimethylacetic, butyric, octoic, nonylic, lauric, methacrylic, fumaric semi-methyl ester, b -dimethylacrylic, phenylacetic, chloropropionic, benzoic, p-chlorobenzoic, p-nitrobenzoic, cyclohexanecarboxylic, furoic, a -bromofuroic, oxalic, adipic, phthalic and terephthalic acids. Examples are given also of the manufacture of the 2,4-dinitro-6-sec.-amylphenyl esters of the following acids: crotonic, acetic, isobutyric, sorbic, a -furoic, benzoic, n-butyric, propionic, acrylic, fumaric semi-methyl ester, dimethylacrylic, 1,3-hexadienic, chloracetic, phenylacetic, chloropropionic, p-chlorobenzoic, oxalic, adipic and phthalic acids. A further example describes the manufacture of 2,4-dinitro-6-tert.-butylphenyl a -(ethylxanthyl) acetate of the formula <FORM:0999876/A5-A6/1>  The products may be mixed with solid or liquid diluents and used in the form of wettable powders, dusts, granulates, pellets, pastes, solutions, emulsions or thermal fumigating mixtures. Experimental results of the use of some of the products are given.