Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1986-03-13
1987-05-26
Raymond, Richard L.
Chemistry: fertilizers
Processes and products
Forms or conditioning
549220, A01N 5724, C07F 940
Patent
active
046682740
DESCRIPTION:
BRIEF SUMMARY
The invention relates to etherified 2-hydroxy-ethyl-phosphonic acid derivatives and plant growth regulating agents containing same as active ingredient. The invention also provides processes for the preparation of the new compounds and the use thereof.
In HU-PS 160,618 as plant growth regulator 2-methoxy-ethyl-phosphonic acid is disclosed.
In Japanese Patent Publication No. 80.111.494 hydroxy-alkyl phosphonic acids substituted by an aromatic group and esters thereof, e.g. 2-(4-chloro-phenyl-oxy)-ethyl-phosphonic acid dimethylester are disclosed and the compounds were mentioned as showing pharmaceutical activity.
Papukova et al. disclosed various phenoxy-alkyl-phosphonic acids and esters thereof in Zsurn. Prikl. Him. (Leningrad) 1972 45 (8) 1808-1818. The activity of the compounds was, however, not mentioned.
The present invention refers to new etherified hydroxy-alkyl-phosphonic acid derivatives of the general formula (I) ##STR2## wherein R stands for 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-, 4-methyl-coumarin-7-yl, 2,2,4-trimethyl-(2H)-chromen-5-yl, or 2,2,4-trimethyl-(2H)-chromen-7-yl, C.sub.1-8 alkyl, C.sub.1-4 halogenalkyl, C.sub.1-4 alkoxy-C.sub.1-2 alkyl and Me stands for a monovalent cation.
The plant growth regulating activity according to the invention means that the new compounds act on the physiological process of the plant growth depending on the time of the use, on the development stage of the plant and on the used active ingredient concentration. Due to the properties of the compounds of the invention they can be utilized in agriculture.
The process for the preparation of the new compounds of the general formula (I) can be characterized by reacting 7-hydroxy-2,3-dihydro-2,2-dimethyl-benzofuran or 7-hydroxy-4-methyl-coumarin or 7-(5)-hydroxy-2,2,4-trimethyl-(2H)-chromene with dihaloethane at a temperature ranging from -10.degree. to +80.degree. C. optionally in the presence of a phase transferring catalyst and reacting the obtained intermediate product, if desired after purification with di- or triethyl-phosphite at a temperature ranging from +40.degree. to +250.degree. C. The temperature range is preferably 100.degree. to 200.degree. C. The reaction is illustrated by reaction scheme E ##STR3##
From compounds of the general formula (I) in agriculture acceptable compositions can be prepared by the addition of carriers, optionally surfactants and water soluble concentrates, dusting agents, wettable powders, granules, emulsifiable concentrates or colloidal aqueous suspensions can be prepared.
When preparing these compositions the active ingredients can be admixed with solid or liquid carriers and surfactants and the blend is optionally homogenized.
The compositions contain 0.1-95% by mass active ingredient and the active ingredients can be used in the form of compositions or solutions, emulsifiable concentrates, suspensions, wettable powders, dusting agents and granules ready to use by pouring, spraying or vapourization. The active ingredient concentration can be varied within a wide range depending on the used active ingredient, on the carriers and/or surfactants.
The preparation of the new compounds and the compositions is illustrated in the following Examples.
EXAMPLE 1
Preparation of 2,3-dihydro-2,2-dimethyl-7-(2'-chloro-ethoxy)-benzofuran
To 100 ml. ethylacetate 8.23 g. (0.05 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran, 14.3 g. (0.1 mole) 1-bromo-2-chloro-ethane, 6.9 g. (0.05 mole) anhydrous sodium carbonate and 8.3 (0.05 mole) potassium iodide are added. The reaction mixture is heated for 30 hours and the reaction is monitored by gas chromatographic analysis.
When the reaction is completed the mixture is cooled to room temperature, the solid is removed by filtration and the solvent is distilled off in vacuo from the solvent layer on a rotatory film evaporator.
The residual yellowish brown oily part is dissolved in 50 ml. methylene chloride and washed with 5.times.30 ml. 5% sodium-hydroxide solution and water. The solvent part is dried above anhydrous sodium sulphate and the s
REFERENCES:
patent: 2159364 (1939-05-01), Coleman et al.
patent: 4042370 (1977-08-01), Trueb
patent: 4560682 (1985-12-01), Horoki et al.
Houben--Weyl, Methoden der Organischen Chemie, vol. 12/1, (1963), p. 437.
B/a/ lint S/a/ ndor
Benczik n/e/ e P/a/ sztor Judit
Csatl/o/ s Imre
Fodor J/o/ zsef
G/a/ rdi Iv/a/ n
Katona Gabriel P.
Nitrok/e/ mia Ipartelepek
Raymond Richard L.
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