DE1670269A1 - New 2- (alpha-phenoxy-acyl) -1,2-O, N-heterocyclo-alkanes - Google Patents

Description

New 2- (α-phenoxy-acyl) -1,2-0, N-heterocyclo-alkanes The present invention relates to new substances of the general formula ~ VIL In this formula: R = hydrogen or lower alkyl, preferably methyl, X = halogen, preferably chlorine or bromine, Y = lower alkyl, preferably methyl, m = the number 0 or 1, - ~ n A is an integer of 1 -3, o = an integer from 2-6, preferably 3 or 4.n preferably represents the number 2 or 3 when m = 0 and the number 1 when m = 1.

The compounds of the above formula have good soil and leaf herbicides Effectiveness against broad-leaved weeds.

The compounds according to the invention can with gaseous, liquid or solid carriers in the generally known formulations, optionally below Addition of emulsifiers, extenders and agents that increase adhesion come into use. The connections can. alone or in mixtures with others known active ingredients are used. Suitable application forms are, for example Suspensions, emulsions or scattering powder.

A suspension powder is obtained, for. B. by the active ingredient with inorganic Filling material such as kaolin, kieselguhr, chalk, and possibly also a little sodium sulfate and whiting, an organic stabilizer (e.g. cellulose ester) and a Wetting agent (e.g. alkyl naphthalene sulfonate) good is ground. the The composition of this suspension powder can be varied within a wide range will. Suitable is z. B. a composition of 20 parts of active ingredient, 20 parts Kaolin P, 43 parts of chalk, 5 parts of sodium sulfate, 2 parts of mud chalk, 1 part wetting agent and 9 parts of a stabilizer. The suspension powder is used suspended in water.

In addition to being in suspension, the substances according to the invention can also can be used in emulsion and as a grit.

An emulsion concentrate is obtained, for example, by mixing of 20 parts of active ingredient, 50 parts of a mixture of aliphatic and aromatic Hydrocarbons, 20 parts of cyclohexanone and 10 parts of a conventional emulsifier.

A scattering powder is obtained, for example. from 1.5 parts of active ingredient, 6 parts Kaolin P and 92 @ 5 parts ~ Ta kum.

N- (2,4-dichloro = phenoxyacetyl) isoxazolidine, for example, is used as a herbicide dispersed in water with the aid of a dispersant and sprayed. Broad-leaved Weeds are completely dead in a short time.

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The preparation of the compounds according to the invention can. by condensation a functional derivative of an appropriately substituted α-phenoxy-alkanecarboxylic acid, for example of the chloride with the 0, N-heterocyclic compound. It is preferred to work in the presence of a base, for example triethylamine. The procedure can be illustrated by the following example: To the mixture of 350 ml of absolute dioxane, 87.5 g (0.40 mol) of 2-methyl-4-chlorophenoxyacetyl chloride and 49.5 g (0.40 mol) of tetrahydro-1,2-oxazine hydrochloride were added with good stirring at first 50 ° 80.8 g (0.80 mol) of triethylamine were added dropwise.

The temperature rose during this. After the end of the dropping The reaction mixture was stirred for 7 hours at 100 ° and then for a further 15 hours Room temperature. The precipitated triethylamine hydrochloride was then filtered off with suction (110 g; 100 $ of theory) and the filtrate concentrated in vacuo to residue.

The oily residue (106 g; 98% of theory) was dissolved in benzene and one after the other with dilute hydrochloric acid, aqueous sodium bicarbonate solution and shaken out again with water. The organic phase was dried with MgSO4 and concentrated in vacuo to a residue. The remaining b1 became crystalline.

Yield: 85 g; 79% d. Th., Recrystallization from isopropyl ether / gasoline.

Mp (after recrystallization): 68-70 °.

Elemental analysis: C: 58.00 s (theor.%).

H: 5.96% (theor. 5.99%) N: 5.42% (theor. 5.20%) Cl: 13.52% (theor. 13.15%).

The following were prepared in an analogous manner: N- (2-methyl-4-chlorophenoxyacetyl) -isoxazolidine, paste-like substance.

N- (2,4-dichloro-phenoxyacetyl) -isoxazolidine, F: 74-75 °.

N- (α- (2,4-dichlorophenoxy) propynyl isoxazolidine, highly viscous 61.

Claims (1)

Claims-1. As new compounds 2- «s-phenoxy-acyl) -1, 2-O, N-heterocycloalkanes of the general formula, in which R is hydrogen or a lower alkyl radical with 1-5 carbon atoms, X is halogen, Y is a lower alkyl radical with 1-5 carbon atoms, m is the number 0 or 1, n is an integer from 1-3 and o is an integer from 2- 6, preferably 3 or 4, where n when m = 0 is preferably 2 or 3 and when m = 1 the number 1'darstelit .. r 2. N- (2-methyl-4-chlorophenoxyacetyl) tetrahydro-1 , 2-oxazine. 3. N- (2,4-dichloro-phenoxyaeetyl) -isoxazolidine. 4. N- (2-methyl-4-chlorophenoxyacetyl) isoxazolidine. 5. NZ "4-dichloro-phenoxy) -propiony ç-isoxazolidine. 6. Herbicidal agents, characterized by a content of compounds of the general formula in which R is hydrogen or a lower alkyl radical with 1-5 carbon atoms, X is halogen, Y is a lower alkyl radical with 1-5 carbon atoms, m is the number 0 or 1, n is an integer from 1-3 and o is an integer from 2- 6, preferably 3 or 4, where n is. m = 0, preferably 2 or 3 and, when m = 1, represents the number 1./ Process for the preparation of compounds of the general formula in which R is hydrogen or a lower alkyl radical with 1-5 carbon atoms, X is halogen, Y is a lower alkyl radical with 1-5 carbon atoms, m is the number 0 or 1, n is an integer from 1-3 and o is an integer from 2- 6, preferably 3 or 4, where n is preferably 2 or 3 when m = O and the counts when m = 1, thereby. characterized in that pan condenses a functional derivative of an appropriately substituted #α-phenoxyalkanecarboxylic acid with the corresponding 0, N-heterocyclic compound in the presence of a base. 8. The method and claim 7, characterized in that the derivative the α-phenoxyalkanecarboxylic acid uses the chloride.