NO153978B - PROCEDURE FOR THE MANUFACTURING OF NAILET TRECELLULOSE FOR CHEMICAL PREPARATION AND SPECIAL PAPER. - Google Patents

Description

Herbicidal preparations.

The present invention relates to new herbicidal preparations which contain as active ingredients selected esters of N-phenyl- or N-m-chlorophenylcarbamic acid.

Certain esters of N-phenyl or N-m-chlorophenylcarbamic acid are known to possess herbicidal properties. Thus, German patent document No. 833,274 discloses that esters of aryl urea acids can be used to destroy weeds and a preferred compound is iso-propyl-N-phenyl-carbamate. German patent no. 1 062 482 discloses herbicidal mixtures and a component thereof is an ester of N-phenyl-, N-m-methylphenyl- or N-m-chlorophenylurea acid where the esterification radical is a saturated or unsaturated alkyl radical containing 1-4 carbon atoms. In the preferred compounds, the esterification radical is butyn-(1)-yl-(3) or isopropyl. More narrowly defined esters of N-phenyl and N-m-chlorophenylurea acids are described as herbicides in British Patent No. 789,445, Swiss Patent No. 360,245 and US Patent Nos. 2,906,614 and 2,857,260.

The present invention provides weed-killing preparations which contain as active ingredient selected esters of N-phenyl- and N-m-chlorophenylcarbamic acid where the esterification radical differs from the esterification radicals present in the previously known herbicides in that they possess an alkoxy substituent. The invention is based on the fact, which could not be predicted, that esters of N-phenyl and N-m-chlorophenylcarbamic acid in which the esterification radical originates from a secondary aliphatic alcohol and contains an alkoxy group, possess particularly valuable weed-killing properties. The patentee has found that compounds of the aforementioned type and which are described in specific terms hereinafter possess valuable selective herbicidal properties, i.e. they can be applied to the soil where the crop and weeds grow to destroy the weeds without damaging the crop. We have also surprisingly found that the crop selectivity properties and the weed control spectrum of the compounds are different from corresponding properties of previously known herbicides with the result that the compounds enable an improved selective weed control, i.e. either a greater safety for the crop and a more effective control of the weeds.

According to the invention, herbicidal preparations have been provided which contain a common herbicidal adjuvant and the preparations are characterized in that they contain as active compound a compound of the general formula I

where Ar means phenyl or m-chlorophenyl, X means methylene or ethylene and Y means an alkoxy group containing up to 4 carbon atoms. The term “common herbicide

"adjuvant" used in this description can be understood to mean any diluent or carrier which can be used for the preparation of preparations containing herbicidal compounds. An adj uwant is thus an aid. Typical adjuvants include dispersing agents, emulsifying agents, wetting agents and powdered, solid diluents. The preparations according to the invention not only include preparations in a suitable form for application to the soil, but also concentrated preparations which. can be supplied to consumers and which requires dilution with an appropriate amount of water or another diluent before use to control weeds.

Typical preparations that fall within the scope of the invention include the following: a) Dispersible solutions. A dispersible solution comprises a solid active ingredient with low water solubility, dissolved in a water-miscible solvent, with the addition of a dispersant, so that an aqueous dispersion is formed when diluted with water. b) Dispersible powders. A dispersible powder comprises a solid active ingredient of low water solubility in association with a dispersing agent, and a solid inert diluent, if

this is desirable, e.g. kaolin.

c) Miscible oils. A miscible oil comprises an active ingredient with lichen

water solubility dissolved in a water-immiscible solvent with the addition of an emulsifier so that an emulsion is formed when diluted with water. Alternatively, consumers can be supplied with a concentrated emulsion which is obtained from a miscible oil by adding a suitably small volume of water. Such concentrated emulsions are diluted with a suitable

amount of water before use.

d) Concentrated suspensions. A concentrated suspension comprises a solid

active ingredient with low water solubility measured into a paste with water

and a dispersant.

e) Dust preparations. A dust preparation or atomizing preparation comprises an active ingredient in association with a solid powder diluent which can be an inert diluent, such as e.g. kaolin, or an aqueous agri-cultural fertilizer. f) Granulated solids. These include an active ingredient united with lig-

nd solid diluents of the kind that can be used in the production of powder-form preparations, but the mixture is granulated using general known methods.

The dispersible solutions, dispersible powders, miscible oils and concentrated suspensions can also contain a wetting agent if desired.

In addition to the ingredients already mentioned, the preparations may contain other common additives which are known in the manufacture of herbicidal preparations. Thus, e.g. preparations to be used for application as pesticides, contain an anti-foaming agent, e.g. liquid paraffin or a silicone liquid.

The preparations may also contain one or more additional herbicidal active ingredients. In particular, they may contain one or more herbicidally active constituents of urea or the triazine group.

Preferably, you should choose a component that does not remain in the soil for too long, e.g. methylmercaptotriazine.

The compounds according to the general formula I have been shown to possess valuable herbicidal properties and can be used for the control of broad-leaved weed species and grass-like weed species. Typical weeds include rye grass, one-year-old meadow sedge (Poa annua), water sedge (Stel-laria media), hen's grass (Polygonum per-sicaria) and sedge (Chenopodium al-bum). Selective weed control in crops such as sugar beet, peas, cabbage, beans, maize, potatoes and plantation crops can be obtained.

The compounds are preferably added before the weeds have emerged from the soil. The supply can only take place on the surface of the earth, e.g. by spraying, or by introduction into the top layer of the soil, e.g. in the top 5 cm of the soil, e.g. by spraying followed by tillage such as e.g. harrowing. In most cases, the addition of the preparations is carried out before both the weeds and the crop have emerged from the soil, but in the meantime the treatment is carried out before the weeds have emerged, but after the crop has emerged from the soil. Some of the compounds can also be used to combat weeds by application after the weeds have germinated or emerged from the soil.

The concentration of the active ingredient in the preparations according to the invention used for weed control depends on the particular composition and the type of machinery used to spread the preparation. In the event that liquid preparations are supplied by spraying, high and low volume spraying devices are usually used to supply the liquid in an amount of from approx. 1/2 to 10 hl per hectares, and this requires preparations containing different concentrations of the active ingredient. From a weed control point of view, it is important to take into account the total amount of the active ingredient applied per unit area of the earth. This dosage will vary from one compound according to the invention to another and also according to the crop and the type of weed to be combated. In general, however, amounts of approx. 1/4 to 50 kg per hectare prove to be effective, and in most cases satisfactory results are achieved with amounts of 1/2 to 5 kg per hectares.

The compounds according to the general formula I are new compounds and they can be prepared by known methods for the preparation of carbamates. The following table lists the melting or boiling points of typical compounds:

The indicated boiling points were measured under reduced pressure, the pressure is given in mm Hg.

The selective herbicidal properties of a representative selection of the compounds according to the general formula I are shown in Table II. The results were achieved by sowing the crops and weeds in bowls in a greenhouse and the soil was immediately sprayed with chemicals, in an amount of from approx. 1/2 kg per hectares to approx. 32 kg per hectares. The effect of the treatment was recorded

by applying the following assessment system:

0: no control at all application quantities 1: control down to 16 kg per hectare 2: control down to 8 kg per hectare 3: control down to 4 kg per hectare 4: control down to 2 kg per hectare 5: control down to 1 kg per hectare 6: control down to 1/2 kg per hectares

The results in another area of weeds and crops using rates of 1/4 to 16 kg/hectare for the near active compounds in Table II are shown in Table III using the following rating system: 0: no control at all application amounts 1: control down to 8 kg/hectare 2: control down to 4 kg/hectare 3: control down to 2 kg/hectare 4: control down to 1 kg/hectare 5: control down to 1/2 kg/hectare 6: control down to 1/4 kg/hectare. In Table IV, the results of experiments similar to those listed in Table II are shown for compounds that do not fall within, but are closely related to, the compounds according to the general formula I, to show the unexpected nature of the valuable selective herbicidal properties of the compounds according to formula I.

Example 1.

2-Methoxy-1-methylethyl chloroformate (15.3 g) in toluene (20 mL) was added dropwise with stirring to a mixture of m-chloroaniline (12.8 g), 5 N -sodium hydroxide (20 ml) and toluene (50 ml) over 45 minutes and the temperature was finally raised to

45°C. The mixture was stirred for an additional 2 hours at room temperature and the upper

solvent layer was separated, dried over anhydrous magnesium sulfate, filtered and

the solvent removed in vacuo. Distillation of the residue gave 2-methoxy-1-methyl-ethyl-m-chlorophenylcarbamate, b.p. 160-170° C/l mm.

Example 2.

A dust preparation was prepared by mixing an active ingredient according to the general formula I (10 parts) with kaolin (90 parts).

Example 3.

A dispersible powder was prepared by mixing an active ingredient according to the general formula I (20 parts), "Belloid T.D." — a medicinal dispersant (8 parts) and kaolin (72 parts).

Example 4.

Preparations suitable for dilution with water to form emulsions were prepared by mixing the following ingredients:

(a)

2-ethoxy-1-methylethyl-N-m-chlorophenylcarbamate 30 weight/dog. "Agrilan A" (a medical

emulsifier) 5 weight/dog. "Ethylan B.V." (a medical

emulsifier) 10.5 weight/dog weight. "Arylan CA." (a medical

emulsifier) 4.5 weight/dog weight. Xylene to 100% by volume.

(b)

2-ethoxy-1-methylpropyl-N-m-chlorophenylcarbamate 30 weight/dog. "Agrilan A" (a medicinal emulsifier) 5 weight/dog weight.

"Ethylan B.V." (a medical

emulsifier) 10.5 weight/dog weight.

"Arylan CA." (a medical

emulsifier) 4.5 weight/dog weight.

Xylene to 100% by volume.

(c)

2-methoxy-1-methylethyl-N-m-chlorophenylcarbamate 40 weight/dog. "Ethylan B.V." 10.5 weight/dog.

"Arylan CA." 4.5 weight/dog.

"Agrilan A" 5 weight/puppy.

Gasoline to 100 vol.

Herbicidal preparations containing a common herbicide adjuvant, characterized in that they contain as active ingredient a compound of the general formula I

where Ar means phenyl or m-chlorophenyl, X means methylene or ethylene and Y means an alkoxy group containing up to 4 carbon atoms.

Claims (1)

Process for the production of a medium to high-viscosity softwood cellulose from a cellulose produced by sulphite digestion, by treatment with NaOH and peroxide and optionally with chlorine, characterized by using 0.01-20% by weight of the amount of chlorine used in the classic bleaching process and /or optionally pre-treats with acid, then by this chlorine treatment it does not or only slightly further delignifies cellulose in a manner known per se to a refinement using alkali at an elevated temperature, and then delignifies with peroxide in an alkaline, aqueous medium so that the main amount of the lignin is removed, and then bleached in a manner known per se in one or more stages.