Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1986-03-13
1988-10-11
Raymond, Richard L.
Chemistry: fertilizers
Processes and products
Forms or conditioning
549220, A01N 5724, C07F 940
Patent
active
047768746
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to 2-chloro-ethyl phosphonic acid esters of the general formula (I) ##STR2## the preparation of said compounds as well as plant growth regulating agents containing as active ingredient the compounds of general formula (I).
In Hungarian patent specification No. 160,618 esters of 2-chloro-ethyl phosphonic acid with pyrocatechol, 4-chloro-pyrocatechol, phenol, salicylic alcohol, salicylic acid, resorcinol and other alcanols are disclosed. The biological activity of the esters is demonstrated on tomatoe, on bean arts, on ananas and on cereals.
In DD-PS No. 132,632 the alkoxy trichloromethyl esters of 2-halo-ethyl phosphonic acid are disclosed having plant growth regulating and desiccant activity.
In U.S. Pat. No. 4,042,370 the cyanoalkyl, alkoxy-carbonyl-alkyl-alkinyl oxo and thio esters of 2-chloro-ethyl phosphonic acid are disclosed which are used for the treatment of rubber trees in order to increase latex crop. In J. Prakt. Chem. 1975 798-806 among others cyclic esters of 2-chloro ethyl phosphonic acid are disclosed and in these esters on the carbon attached to the oxygen can be hydrogen, alkyl or a cycloalkylene group can be attached to the two oxygen atoms.
The new 2-chloro-ethyl phosphonic derivatives can be characterised by the general formula (I) wherein C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy-C.sub.1-2 alkyl or a monovalent cation, 4-methyl-coumarin-7-yl, 2,2,4-trimethyl-(2H)-chromen-5-yl or 2,2,4-trimethyl-(2H)-chromen-7-yl, Me stands for a monovalent cation and represents the salt of the acid.
The compounds of the 2-chloro-ethyl-phosphonic acid esters can be prepared by reacting the corresponding benzofuran or coumarin or chromene derivative with 2-chloro-ethyl-phosphonic acid dichloride in the presence of an acid binding agent. When preparing the diesters the corresponding benzofuran, coumarin or chromene derivative and the alcanol are reacted in the presence of an acid binding agent, and the desired end-product is isolated by methods known per se.
The salts of the 2-chloro-ethyl phosphonic acid esters can be prepared by reacting the diester without isolation with the corresponding metal hydroxide.
From the active ingredients of the general formula (I) the usual compositions such as water-soluble concentrates, wetting agents, wettable powders, granules, emulsifyable concentrates, colloidal aqueous suspensions can be prepared.
The plant growth regulating activity means an activity of the active ingredient on the physiological processes of the plant growth depending on the time of the use, on the development stage of the plant and on the used concentration.
The compositions can be prepared by methods known per se such as admixing the active ingredients with carriers i.e. liquid solvents and/or solid carriers and optionally surfactants, such as emulsifying or dispersing agents can be used.
The compositions contain 0.1-95% by mass active ingredient. The active ingredients are usually used in the form of compositions or they can be used in the form of solutions, emulsifyable concentrates, suspensions, wettable powders, dusting agents or granules by spraying or vapourization. The active ingredient concentrations can be varied within a wide range depending on the character of the used active ingredients.
The new active ingredients and the compositions prepared from the active ingredients are illustrated in the following Examples.
EXAMPLE 1
Preparation of 2-chloro-ethyl-phosphonic
acid-O-(2,3-dihydro-2,2-dimethyl-benzofuran-7-yl)-monoester
(Compound No. 1)
To 70 ml. anhydrous benzene 16.42 g (0.1 mole) 2,3-dihydro-2,2-dimethyl-7-hydroxy-benzofuran and as acid binding agent 12.11 g. (0.1 mole) N,N-dimethyl-aniline are added whereafter 21.93 g. (0.12 mole) 2-chloro-ethyl-phosphonic acid dichloride are added dropwise to the reaction mixture at room temperature under stirring. The reaction mixture is then heated for 2 hours and the reaction is monitored by gas chromatographic analysis.
When the reaction is completed the mixture is cooled and at 20.degree.-30.degree. C. a s
REFERENCES:
patent: 4042370 (1977-08-01), Trueb
patent: 4560682 (1985-12-01), Hiroki et al.
patent: 4668274 (1987-05-01), Balint et al.
Houben-Weyl, Methoden der Organischen Chemie, vol. 12/1 (1963) pp. 417, 418, 423 & 424.
Balint Sandor
Benczik nee Pasztor Judit
Csatlos Imre
Fodor Jozsef
Gaal Sandor
Nitrokemia Ipartelepek
Raymond Richard L.
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