Patent GB-671153-A (GB)
Title: Improvements in plant growth regulants and phytocides
IPC: C07D209/48
Filed: 1950-02-22
Abstract: N-arylphthalmic acids are prepared by reacting phthalic anhydride with a primary or secondary mono-acylamine.  The secondary mono-acylamine may be N-substituted by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, amyl, hexyl or octyl.  The N-aryl group of the phthalmic acid may be o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, 2,4 - dichlorophenyl, 2,5 - dichlorophenyl, 2,4,5 - trichlorophenyl, 2 - methyl - 4 - chlorophenyl, 2 - bromophenyl, 4 - bromophenyl, 2,4,5-tribromophenyl, o-, m- or p-nitrophenyl, 2 - methyl - 4 - nitrophenyl, 2 - chloro - 4-nitrophenyl, o-, m- or p-hydroxyphenyl, 2-chloro - 4 - hydroxyphenyl, o - m - or p - tolyl, or a - or b -naphthyl.  The reaction may be effected by stirring the reactants together at room temperature in a solvent such as benzene, xylene or kerosene.  The phthalmic acids may be converted into their esters, e.g. methyl, ethyl, propyl, or butyl esters or their salts, e.g. their sodium, potassium, ammonium, methylammonium, dimethyl ammonium, trialkyl ammonium, ethyl ammonium, ethanol ammonium, diethanol - ammonium or triethanol ammonium salts.  The N-arylphthalmic acids which originate from primary mono-acylamines may be heated to 80-180 DEG  C. to form the corresponding N-aryl phthalimides.ALSO:A plant growth regulant composition comprises as an active ingredient a N-aryl phthalmic acid or a N-aryl phthalamide, and also a surface-active dispersing agent and/or a solid powdered carrier.  The phthalmic acid may also be N- substituted by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, amyl, hexyl or octyl.  The N-aryl group of phthalmic acid or phthalamide may be o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, 2, 4-dichlorophenyl, 2, 5-dichlorophenyl, 2, 4, 5-trichlorophenyl, 2-methyl-4-chlorophenyl, 2-bromophenyl, 4-bromophenyl, 2, 4, 5-tribromophenyl, o-, m- or p-nitrophenyl, 2-methyl-4-nitrophenyl, 2-chloro-4-nitrophenyl, o-, m- or p-hydroxyphenyl, 2-chloro-4-hydroxyphenyl, o-m- or p-tolyl, or   or b -naphthyl.  The phthalmic acids may be in the form of the free acids, their esters, e.g. methyl, ethyl propyl, or butyl esters or their salts, e.g. their sodium, potassium, ammonium, methylammonium, dimethyl ammonium, trialkyl ammonium, ethyl ammonium, ethanol ammonium, diethanol-ammonium or triethanol ammonium salts.  Specified solid carriers are mica, talc, pyrophyllite, and clays.  Specified dispersing agents are soaps, alkyl sulphates or sulphonates, sulphonated or sulphated aliphatic ethers, sulphonated alkyl esters of long chain fatty acids, sulphonated glycol esters of long chain fatty acids, sulphonated alkyl substituted amides of long chain fatty acids, alkylated aryl sulphonates, hydroaromatic sulphonates, alkyl sulphosuccinates, aryl sulphonate-formaldehyde condensation products, polyether alcohols, polyglycol esters, partial esters of polyhydric alcohols with long chain fatty acids, quarternary ammonium salts one of the N- substituents of which is an aliphatic group containing at least 8 carbon atoms, and amines, amides, diamines and glyoxalidines having an aliphatic group containing at least 8 carbon atoms.