ES209289A1 - New oxazoline derivatives - Google Patents

Abstract

The invention comprises oxazoline derivatives of the formula <FORM:0730192/IV (b)/1> where R and R1 stand for hydrogen or lower alkyl radicals and the phenyl nucleus A is substituted by at least one halogen atom and may also bear further halogen and/or alkyl radicals of not more than 4 carbon atoms. Preferably the phenyl nucleus is substituted by at least two halogen atoms as in 2-(31 : 51-di-chloro - 21 - hydroxyphenyl) oxazoline and 2 - (31 : 51 - dibromo - 21 - hydroxyphenyl) oxazoline. The compounds are made by (A) reacting a 2-hydroxybenzoic-b -hydroxyethylamide of the formula <FORM:0730192/IV (b)/2> with a dehydrating agent such as phosphorus pentoxide, phosphorus oxychloride, phosphorus trichloride, thionyl chloride or sulphuric acid (B) reacting an o-hydroxybenziminoether of the formula <FORM:0730192/IV (b)/3> where R11 is an alkyl radical of not more than 4 carbon atoms with a b -aminoalcohol of the formula NH2.CHR.CHR1OH and if necessary heating the reaction product to give the oxazoline derivative (C) halogenating an oxazoline derivative of the formula <FORM:0730192/IV (b)/4> wherein the phenyl nucleus B may optionally be substituted by alkyl radicals of not more than 4 carbon atoms and/or halogen atoms provided that at least one of the 31 and 51 positions is unsubstituted (D) reacting a compound of the formula <FORM:0730192/IV (b)/5> with a compound of the formula NH2-CHR-CHR1-OH in the presence of a halide or oxyhalide of phosphorus and (E) reacting an o-hydroxybenzoic-allylamide of the formula <FORM:0730192/IV (b)/6> with a concentrated mineral acid to give products in which R stands for hydrogen and R1 is a methyl radical. Examples describe the preparation by the above methods of (2) 2-(41-chloro - 2 - hydroxyphenyl) oxazoline 2 - (51 - chloro-21-hydroxyphenyl) oxazoline 2-(31 : 51 dichloro - 21 - hydroxyphenyl) oxazoline 2 - (31 : 51 - dibromo - 21 - hydroxyphenyl) oxazo line 2 - (31 : 51 - diiodo - 21 - hydroxyphenyl oxazoline 2 - (31 : 51 - dichloro - 21 - hydroxyphenyl) - 5 - methyloxazoline, and 2 - (51 - chloro-21-hydroxyphenyl)-5-methyloxazoline.ALSO:Fungicidal and acaricidal compositions contain as the active ingredient oxazoline derivatives of the formula <FORM:0730192/VI/1> where R and R1 are hydrogen atoms or alkyl radicals of not more than four carbon atoms and the phenyl nucleus is substituted by at least one halogen atom and may be substituted by further halogen atoms or alkyl radicals of not more than four carbon atoms. The compositions may suitably be powders self-dispersible in water comprising one or more of the oxazoline derivatives and one or more wetting, spreading or dispersing agents which may also contain an inert pulverulent diluent, or they may be oils, self miscible in water, comprising one or more oxazoline derivatives with wetting, spreading or dispersing agents. In examples compositions are described comprising (12) a powder dispersible in water containing 2-(31:51-dichloro - 21- hydroxyphenyl) oxazoline and dinaphthylmethane disulphonic acid sodium salt (13) a powder containing 2- (31 : 51- dichloro - 21- hydroxyphenyl)- oxazoline, the sodium salts of dinaphthylmethane disulphonic acid and isopropylnaphthalenesulphonic acid and china clay (14) a dispersible powder prepared by intimately mixing 2- (31 : 51- dichloro - 21- hydroxyphenyl) oxazoline, the sodium salt of dinaphthylmethane disulphonic acid, the condensation product of cetyl alcohol and ethylene oxide, triisopropylnaphthalenesulphonic acid and water, evaporating to dryness and grinding the solid product and (15) a dispersion made by mixing 2 - (31:51 - dibromo - 21- hydroxyphenyl) - oxazoline, diacetone alcohol and the condensation product of cetyl alcohol and ethylene oxide and pouring into water. Many other oxazolines are specified (see Group IVb).