Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1987-01-30
1989-07-11
Lone, Werren B.
Chemistry: fertilizers
Processes and products
Forms or conditioning
560193, 560194, A01N 3700, C07C 6940
Patent
active
048468835
DESCRIPTION:
BRIEF SUMMARY
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-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).
British patent specification No. 1,491,308 discloses various .beta.-phenoxyethyl and .beta.-phenylthioethyl carboxylates as fungicides; one of them being .beta.-phenoxyethyl succinate.
Now it has been found that certain mono- and di-(aryloxyethyl)succinates and agriculturally acceptable salts thereof possess excellent plant growth regulating properties superior to those of the known substances of related structure.
Based on the above, the invention relates to mono- and di-(aryloxyethyl)succinates of the formula (I), ##STR5## wherein A represents hydrogen, a naphthoxyethyl group of formula (b), ##STR6## or a substituted phenoxyethyl group of the formula (a), ##STR7## and in this latter formula R stands for hydrogen or C.sub.1-4 alkyl, hydrogen,
The invention also relates to agricultural, primarily plant growth regulating compositions, comprising as active agent at least one compound of the formula (I).
In the above formula the term "alkyl" means preferably methyl, whereas "halo" means preferably chloro. Substituents R.sup.1, R.sup.2 and R.sup.3 are attached to the phenyl ring preferably in positions 2 and/or 4 and/or 5.
The invention also relates to a process for the preparation of compounds having the formula (I) with the exception of .beta.-phenoxyethyl succinate.
The compounds of the formula (I) are prepared according to the invention by reacting succinic anhydride of formula (II) ##STR8## with an aryloxy ethanol of the formula (III), ##STR9## wherein A is as defined above.
Depending on whether a mono or a diester is required, the alcohol of the formula (III) is utilized in amounts of essentially 1 or 2 molar equivalents. The reaction is performed in the presence of a mineral acid, such as concentrated sulfuric acid, as catalyst.
The reaction is performed preferably in a solvent, such as in a chlorinated hydrocarbon (e.g. carbon tetrachloride), a ketone (e.g. methyl-ethyl ketone) or in a mixture thereof, or in an aromatic hydrocarbon (e.g. benzene).
Water formed in the diesterification reaction should be removed continuously from the system e.g. by utilizing a Marcusson apparatus.
The reaction temperature may be as high as the boiling point of the mixture. It is preferred to perform the reaction in a refluxing mixture.
The resulting product can be separated and, if necessary, purified by methods known per se.
The salts oof the monoesters may be salts formed with inorganic or organic bases, such as alkali metal salts, alkaline earth metal salts or salts formed with organic amines. These salts can be prepared by methods known per se.
Depending on whether a mono- or a diester is to be prepared, one proceeds e.g. as follows:
Succinic anhydride is suspended in carbon tetrachloride or in a mixture of carbon tetrachloride and methyl ethyl ketone, 1-2 drops of sulfuric acid are added to the suspension, the mixture is heated to reflux temperature, and one molar equivalent of the appropriate aryloxy alcohol of the formula (III) is added dropwise to the boiling suspension under stirring within one hour. Thereafter the mixture is stirred and refluxed for 1-3 hours. The mixture is allowed to cool, the separated monoester is filtered off, washed with water or aqueous alcohol, and dried at a temperature not exceeding 40.degree. C.
When a diester is to be prepared, succinic anhydride, 2 molar equivalents of the appropriate aryloxy ethanol and 15-20 drops of sulfuric acid are added to an aromatic solvent, such as benzene. The mixture is stirred and refluxed for 5-15 hours in a flask equipped with a Marcusson appar
REFERENCES:
patent: 2765224 (1956-10-01), Lambrech
patent: 3085078 (1963-04-01), Fath
patent: 4036984 (1977-07-01), Takahashi et al.
patent: 4456721 (1984-06-01), Halpern
Belai Ivan
Buban Tamas
Gerlei Aniko nee Komaromy
Kerekes Gyula
Kovacs Magda, nee Kalman
Clarke Vera C.
Dubno Herbert
Lone Werren B.
Myers Jonathan
Reanal Finomvegyszergyar
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