Patent GB-851907-A (GB)
Title: Substituted dinitrophenyl pentenoates
IPC: C07C205/43
Filed: 1957-05-28
Abstract: The invention comprises compounds of the general formula ; <FORM:0851907/IV(b)/1> where one of the groups R1 and R2 is a nitro group and the other is a C4-C10 hydrocarbon group which is an aryl, aralkyl, or saturated aliphatic or cycloaliphatic group. Suitable hydrocarbon substituents are butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, 2-ethylbutyl, heptyl, octyl, 2-octyl, nonyl, 3,5,5, trimethyl-hexyl, decyl, cyclohexyl, methylcyclohexyl, trimethylcyclohexyl, phenyl, methylphenyl, benzyl or methylbenzyl. The compounds of the invention may be prepared by reacting a -4-pentenoyl halide with a dinitro, hydrocarbon substituted, phenate in the presence of an inert solvent such as a low boiling naphtha at 10 DEG  to 80 DEG C. or more, and the solvent solution of the product treated with water or alternatively by reacting a hydrocarbon substituted dinitrophenol with a tertiary amine such as triethanolamine, benzydimethylamine, pyridine, triethylamine or triamylamine in the presence of an inert organic solvent such as naphtha or toluene, and treating the resulting phenate at 10 DEG  to 50 DEG C. with 4-pentenoyl chloride or bromide the reaction being allowed to proceed with control by temperature between 10 DEG  and 160 DEG C. and being completed at a temperature between 20 DEG . and 100 DEG C.  Thea mine hydrohalide is washed out with water and the product worked up.  The 4-pentenoyl halides may be prepared from lower alkyl esters of 4-pentenoic acid.  Examples are given of the preparation of 2, 4-dinitro-6-cyclohexyl-phenyl 41-pentenoate ; 2, 6-dinitro-4-cyclohexylphenyl 41-pentenoate ; 2, 4-dinitro-6-methyl-heptylphenyl-41-pentenaoate ; 2, 6,-dinitro-4-(1,1,3,3, tetramethylbutyl)-phenyl -41-pentenoate, 2, 6, dinitro-4-decylphenyl-41-pentenoate, 2, 4, dinitro-6-decylphenyl -41-pentenoate, 2, 6, dinitro-4-tert-butylphenyl-41-pentenoate 2, 6,-dinitro-4-tert-amyphenyl 41-pentenoate, 2, 4 dinitro-6-phenylphenyl 41-pentenoate.  These compounds may be used as pesticides.ALSO:Fungicidal, miticidal, bactericidal and insecticidal compositions contain as active ingredients, compounds of the general formula:  <FORM:0851907/VI/1> where one of the groups R1 and R2 is a nitro group and the other is an aryl, aralkyl, or saturated aliphatic or cycloaliphatic hydrocarbon group of 4-10 carbon atoms together with a solid or liquid carrier.  Suitable hydrocarbon substituents are butyl, tertbutyl, amyl, isoamyl, tert-amyl, hexyl, 2-ethylbutyl, heptyl, octyl, nonyl, 3,5,5, trimethyl-hexyl, decyl, cyclohexyl, methylcyclohexyl, trimethylcyclohexyl, phenyl, methylphenyl, benzyl or methylbenzyl.  Suitable carriers for preparing dusts are clay, diatoriaceous earth, pyrophyllite, talc, or walnut shell flour.  A dispersing agent such as sodium lignin sulphonate or condensed formaldehyde-naphthalene sodium sulphonate may be present.  Wettable powders may also be used. The compounds of the invention may also be used in a solvent, such as acetone, or by preparing an emulsifiable concentrate by solution in a compound such as toluene, xylene, or an aromatic naphtha and including a solvent-soluble emulsifier.