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2-Alkenyl and 2-alkynyl succinic acid(cas:110-15-6) N-(3,5-dichlorophenyl)imides
Release time:2016/8/22 17:07:24

2-Alkenyl and 2-alkynyl succinic acid N-(3,5-dichlorophenyl)imides

The invention relates to fungicidally active compositions that contain at least one compound of the general formula ##STR1## and/or a compound of the formula ##STR2## in which: A denotes the --CHCH-- or --C.tbd.C-- group and R1 and R2 represent hydrogen or methyl.

The active substances according to the invention can be obtained by reacting correspondingly substituted succinic acids(cas:110-15-6), or acid halides, anhydrides or esters thereof, with 3,5-dichloroaniline.

Preparation of 2-allylsuccinic acid N-(3,5-dichlorophenyl)-imide

28 g (0.2 moles) of allylsuccinic acid anhydride, 32.4 g (0.2 moles) of 3,5-dichloroaniline, 0.6 g of triethylamine and 150 ml of xylene are reacted at 125° C., with stirring. The water produced during the reaction is removed azeotropically by way of a water separator. The duration of the reaction is 4 hours. The solvent is subsequently drawn off and the residue is recrystallized from ethyl acetate with the addition of active carbon. The product has a melting point of 121° C. The yield is 89.4% of the theoretical yield.

Preparation of 2-allyl-3-methylsuccinic acid(cas:110-15-6) N-(3,5-dichlorophenyl)-imide
90.5 g (0.5 moles) of 2-allylmalonic acid diethyl ester are reacted in diethylene glycol dimethyl ether with 0.5 moles of alcohol-free sodium ethoxide. 0.5 moles of 2-bromopropionic acid ethyl ester is added dropwise to this solution, with stirring. The mixture is heated for a further 2 hours under reflux and the solvent is then removed. The residue is subsequently subjected to hydrolysis in alcoholic KOH. After drying the organic layer that has separated, it is fractionated. The desired 2-allyl-1-methylethane-tricarboxylic acid 1,2,2-triethyl ester boils under 0.02 torr at 92° to 95° C. The ester is hydrolyzed in alcoholic KOH and, after working up in the customary manner, is decarboxylated at 170° C. with water being split off. The anhydride of 2-allyl-3-methylsuccinic acid(cas:110-15-6) (b.p. at 0.1 torr: 108° to 110° C.) is obtained in a 96% yield (based on the ester).
The anhydride is reacted with 3,5-dichloroaniline as described in Example 1.

The desired product has a melting point of 131° C.

3-Methylenecyclobutane-1,2-dicarboxylic acid N-(3,5-dichlorophenyl)-imide.
In a steel autoclave of 2 liters capacity, equipped with a stirrer, 500 g (5.1 moles) of maleic acid anhydride, 645 ml of benzene and 0.25 g of hydroquinone are cooled to -70° C., with stirring. After evacuation to 20 torr, 100 g (2.5 moles) of allene are drawn into the autoclave by suction. The reaction mixture is then heated to 200° C., with stirring. After 8 hours, the reaction mixture is cooled to 25° C., relieved of pressure, and unreacted allene is collected in a cold trap. The benzene solution is decanted off and the residue is dissolved in 500 ml of acetone. The combined benzene and acetone solutions are subsequently worked up by distillation. After removing the solvents, up to 250 g of maleic acid anhydride are recovered at between 110° and 115° C. under a pressure of 40 torr. Finally, 119 g of the crude product of the desired anhydride are obtained under 3 torr in a fraction boiling at 70° to 125° C. The crude product is subsequently rectified under 25 torr at 155° to 159° C. The yield is 25%.

The anhydride is reacted with 3,5-dichloroaniline as described in Example 1. The resulting product has a melting point of 119° C.

Grape Juice Test
20 ml of a nutrient solution consisting of grape juice and distilled water in a weight ratio of 1:1 are poured into glass petri dishes and the active substances listed in Table 1 are added thereto in the stated concentrations. Each test mixture is then inoculated with 50 μl of a suspension of Botrytis spores, prepared by washing the Botrytis spores from an agar culture with distilled water.
After incubation periods of 10 to 20 days, respectively, at 20° C., the extent of fungal development on the surface of the nutrient solution is assessed.

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