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New succinic acid derivatives of the formula wherein A represents hydrogen, a naphthoxyethyl group of formula (b), or a substituted phenoxyethyl group of the formula and in this latter formula R stands for hydrogen or C1-4 alkyl,R1 is hydrogen, halo or C1-4 alkyl, andR2 and R3 each stand for hydrogen or halo,and agriculturally acceptable salts thereof are prepared by reacting succinic anhydride with an aryloxyethanol of the formula The new succinic acid(cas:110-15-6) drivatives of the formula possess plant growth regulating properties.
The invention relates to new mono- or di-(aryloxyethyl)-succinates and plant growth regulating compositions containing these compounds. The invention also relates to a process for the preparation of new mono- or di-(aryloxyethyl)succinates.
Succinic acid(cas:110-15-6)-2,2-dimethyl-hydrazide (daminozide) is a well known compound utilized as active ingredient in plant growth regulating compositions (Alar-85 WP; see: Louis G. Nickell: Plant Growth Regulators Agricultural Uses; Springer Verlag, Berlin-Heidelberg-New York, 1982).
EXAMPLE 1
(2-Methyl-2-(2',4',5'-trichlorophenoxy)-ethyl)succinate16 g (0.16 mole) of finely powdered succinic anhydride are added to a mixture of 250 ml of dry carbon tetrachloride and 50 ml of methyl ethyl ketone. The mixture is heated to reflux, and a solution of 40.9 g (0.16 mole) of 2-methyl-2-(2',4',5'-trichlorophenoxy)-ethanol in 50 ml of methyl ethyl ketone is added dropwise to the stirred mixture within one hour. Thereafter the mixture is stirred and refluxed for one hour. The mixture is allowed to cool, the product is filtered off with suction, admixed with about 3 volumes of 80% aqueous methanol, and filtered. The product is dried at 40° C. 27.2 g (47.8%) of the title compound are obtained.
EXAMPLE 2
Di-(β-naphthoxyethyl)succinate
50 g (0.5 mole) of succinic anhydride, 188 g (1 mole) of β-naphthoxy-ethanol and 10 drops of concentrated sulfuric acid are added to 300 ml of dry benzene. The reaction mixture is stirred and refluxed for 8 hours under a Marcusson water separator. The mixture is allowed to cool, the separated product is filtered off by suction, washed with water, then three times with an aqueous sodium carbonate solution, and finally with water again. The product is dried at room temperature. 171 g (74.7%) of the title compound are obtained.
EXAMPLE 3
Phenoxyethyl succinate
250 g (2.5 moles) of finely powdered succinic anhydride and two drops of concentrated sulfuric acid are added to 300 ml of dry carbon tetrachloride. The mixture is heated to boiling, and then 345 g (2.5 moles) of phenoxyethanol are added dropwise to the stirred mixture within one hour. The resulting mixture is stirred under reflux for one hour, and then allowed to cool. The separated product is filtered off by suction, washed with water, and dried at room temperature. 583 g (98%) of the title compound are obtained.
The compounds of the formula prepared according to the invention are summarized in Table I.
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