Patent GB-1005858-A (GB)
Title: Fungicidal compositions and nitroalkyl esters for use therein
Inventor: BEAVER DAVID JOHN
IPC: C07C205/40
Filed: 1962-08-20
Abstract: The invention comprises nitroalkyl esters of monocarboxylic acids having the general formula Z-CO-OR in which R is a nitro-substituted alkyl group having 2-6 carbon atoms, the nitro group being bonded to a carbon atom other than that which is bonded to the carboxyl group, and Z is (a) a group of the general formula R1R2R3C-in which R1, R2 and R3\h are like or unlike C1-C3 alkyl groups or (b) an alkanoyl group having 2-7 carbon atoms, or (c) an alkanoylalkyl group having 3-7 carbon atoms. These new nitroalkyl esters and those in which Z is in general a hydrocarbon group having 1-17 carbon atoms may be prepared by reacting the corresponding acid halide with a nitro-substituted alkanol ROH preferably at a temperature in the range 10-120 DEG  C. and optionally in the presence of an organic solvent, e.g. acetone. When Z is an alkanoyl group the esters are most conveniently prepared by heating the corresponding ketocarboxylic acid or an alkyl ester thereof with ROH in the presence of an esterification catalyst such as p-toluene sulphonic acid.  When Z is a hydrocarbon group it may be a saturated or unsaturated aliphatic or cycloaliphatic group, an aromatic group, a partially hydrogenated polycyclic aromatic group or a bridged ring group. Details are given of the preparation of a large number of the nitro esters.ALSO:A fungicidal composition comprises a nitroalkyl ester of a monocarboxylic acid having the general formula Z-CO-OR, in which R is a nitro substituted alkyl group having 2-6 carbon atoms, the nitro group being bonded to a carbon atom other than the one bonded to the carboxyl group and Z is a hydrocarbon group having 1-17 carbon atoms, an alkanoyl group having 2-7 carbon atoms or an alkanoylalkyl group having 3-7 carbon atoms, together with a finely divided solid or liquid diluent.  Z may be, for example, a saturated or unsaturated aliphatic or cycloaliphatic hydrocarbon group, an aromatic hydrocarbon group, a partially hydrogenated polycyclic aromatic hydrocarbon group or a bridged ring hydrocarbon group. Examples of suitable alkyl groups are those in which Z is R1R2R3C-, in which R1, R2 and R3 are the same or different and are C1-C3 alkyl groups.  The nitroalkyl esters may be used as solutions, suspensions or emulsions in organic liquids, e.g. isopropyl ether, acetone, methyl ethyl ketone, dioxane, cyclohexanone, carbon tetrachloride, ethylene dichloride, tetrachloroethane, hexane and higher alkanes, hydrogenated napthalenes, and various hydrocarbon fractions.  When used in the form of an aerosol the active ingredient is dissolved in a suitable solvent and the resulting solution in a chlorofluoroalkae. The nitroalkyl esters may be dispersed in solid carriers, e.g. tricalcium phosphate, calcium carbonate, kaolin, bole, kieselguhr, talc, bentonite, fullers' earth, pyrophillite diatomaceous earth, calcined magnesia, volcanic ash, sulphur, powdered cork, powdered wood or powdered walnut shells. The esters may also be dispersed in a semi-solid extending agent such as petrolatum or soap with or without the acid of solubility promoters and/or surfactants or dispersing agents.  Water-soluble surfactants may also be added to solutions of the esters in organic solvents.  The esters may be used together with other pesticides, nematocides, bacterocides and herbicides.