KR810001031B1 - Process for the preparation of n'-(4-(substituted phenethyloxy)phenyl)-n-methyl-n-methoxyurea - Google Patents

Abstract

Title ureas (I; X1 = H, Me; X2 = C1-5 alky) were prepd. by the reaction of 4-phenethyloxyphenylisocyanate(II) and N, O-dimethylhydroxylamine. Thus, 5.5 g 4-(4-methylphenethyloxy) isophenylcyanate was treated with 2 g N, O-dimethylhydroxylamine soln. to give 7.4 g N'-[4(4-methylphenethyloxy) phenyl -N-methoxy-N-methylurea (m.p. 82-83oC).

Description

Preparation of N '-[4- (substituted phenethyl phenyl) -N-methyl-N-methoxy urea

General formula:

N '-[4- (substituted phenethyl phenyl) -N-methyl-N-methoxy urea in which X ₁ is a hydrogen atom or a methyl group, X ₂ is C ₁ -C ₅ alkyl, or C ₁ -C ₅ alkoxy groups have significant herbicidal activity against a wide variety of weeds in the cultivation of soybeans, peanut cotton, corn, wheat or rice, without material toxicity to mammals, fish and crops.

The present invention, general formula:

N '-[4- (substituted phenethyl phenyl) -N-methyl-N-methoxy urea (hereinafter referred to as substituted ureas). [Wherein X ₁ is a hydrogen atom or a methyl group, X ₂ is C ₁ -C ₅ alkyl (eg methyl, ethyl, propyl, butyl, pentyl) or a C ₁ -C ₅ alkoxy group (eg Methoxy, ethoxy, propoxy, butoxyphen, oxy], and the preparation and use thereof.

As is well known, soybeans, peanuts, cotton, maize, wheat and rice are important crops worldwide. The chemical management of weeds in the cultivation of these crops is absolutely necessary to prevent a reduction in harvest. As is well known, among the substituted urea derivatives are N'-4-chlorophenyl-N, N-dimethyl urea (monutone) and N'-3,4-dichloro phenyl-N, N-dimethyl urea (diutone). There are compounds with strong herbicidal activity such as).

It is also well known that the production of these urea derivatives is due to the inhibition of photosynthesis.

Photosynthesis is a unique physiological action on higher plants and does not work on mammals.

Thus, the specific inhibitors of photosynthetic manipulation do not cause significant damage to mammals, but are likely to eradicate higher plants.

In fact, photosynthetic inhibitors for herbicides such as monuron, diuron, 5-bromo-3- 2-butyl uracil (broomasil) isotropics are all low toxicity to mammals.

However, photosynthesis is common to higher plants, so they exert herbicidal action on all higher plants.

As a matter of fact, almost all photosynthetic inhibitors are non-selective and cause damage to crop plants.

To be a selective herbicide, the compound must have both a strong herbicidal action on the weeds and a high standard of selectivity for the planned crop.

However, such selective herbicides are very difficult to find and cannot be easily organized systematically only by the similarity and changes in chemical composition known to the public. Therefore, it is necessary to find these selective herbicides in a very detailed study with trial and error. For example, in the case of 2-chloro-4-ethylamino-6-isopropyl amino-S-troazine (atrazine) with high selectivity to corn, the chlorine atom in the 2-position is important for selectivity.

Compounds with either methoxy or methylthio groups instead of chlorine atoms have very low selectivity for corn. [H. Gysin: Chemistry of Pesticides, Vol. 5, pp. 1 to 27 (1972), and chemical structure and biological relationship of S-triazines.

N'-3,4-dichlorophenyl-N-methoxy-N-methyl urea (Linutone) has selectivity for some crops, such as carrots, but compounds with methyl groups instead of methoxy groups are identical. (Pesticides Handbook of the Weed Science Society of America, 3rd Edition, pp. 172-176 and pp. 221-225 (1974)).

Selective herbicidation requires a very specific chemical structure, so that very small differences in chemical structure make a big difference in the degree and type of selectivity. The present inventors have decided to focus on phenyl urea derivatives in view of low toxicity in mammals and strong action of herbicides, and have investigated in depth how to give selectivity to these derivatives.

As a result, the substituted urea (I) exhibited strong herbicidal activity against many types of weeds by inhibiting photosynthesis, and in addition to the use of soil in cotton and wheat and in both soil and leaves, Peanuts, corn and rice were found to be highly selective.

While there are large numbers of selective herbicides in the herbicides used in the soil, there are only a few selective herbicides in the leaves.

The remarkable nature of the substituted ureas (I) thus depends on the fact that their use in leaves is selective for soybeans, peanuts, corn and rice, and at the same time shows strong herbicidal activity against a wide range of weeds.

To describe in more detail the herbicidal action of substituted ureas (I), these herbicides have a strong herbicidal effect on the weeds and paddy field weeds in a wide range of alpine fields, both before and after the emergence of weeds.

For example, broad-leaved weeds such as Amaranthus retroflexus, Chenopodium alubum Xanthium pennsylvanicum, Ipomoeapurpurea, Stellaria media, Radishes Raphanus sativus, Polygonum lapathifolium, Rothala indica, Monarch squirrel (Monochoria vaginalis), Field grass (Linderna pyxidaria), Pitten hawk (Sidnum frondosa), Solanum nigrum, Sunflower (Heliantbus annus) , Datura stramonium, Abutilon theophrasti, etc. Grassy weeds, for example, Eleusine indica, Digitaria sanguinalis, Echinochloa crus-galli, Puppy grass (Setaria viridis) ), And the like, pulps Seeds show strong herbicidal activity at low concentrations in various weeds such as Cyperus difformis and the like. Substituted ureas (I) as described above are selective for soybeans, peanuts, corn, and rice by use in soil and cotton and wheat, and in both soil and leaves.

Therefore, they are useful as selective herbicides for major crops such as soybeans, cotton, peanuts, corn, wheat and rice.

In addition, they can be used as herbicides for pastures, orchards, groves and forests, and non-cultivated lands, using their broad herbicide spectrum.

In addition, the toxicity of lower mammals and fish is one of the properties of substituted urea (I).

Substituted ureas (I) are novel in themselves, but there are several compounds known to the general public in their chemical composition.

For example, N '-(3-chloro-4-benzyl oxyphenyl) -N-methoxy-N-methyl urea is disclosed in Swiss Patent No. 532, 891.

However, this patent does not explain the selectivity of this compound for legumes and cotton.

According to the experiments of the present inventors, this compound shows strong phototoxicity against soybean by use on leaves as shown in Examples I and V described below.

One of the biggest properties of substituted ureas (I) is that they can be used as selective preparations on the leaves at the top of soybean crops in their fields. N'-4- (4-chlorophenoxy) phenyl-N, N-dimethylurea (chloroxuron), 3-isopropyl-1H-2, 1,3-benzothiadiazine-4 (3H) -one-2,2-2 oxide (bentazone) is illustrated.

Chlorocyclone tends to be phototoxic to soybeans, so great care must be taken to prevent it. [Weed Management of Soybeans from the Mississippi Cooperative Extension Service (1974), Mississippi State University's 1976 Weed Management Recommendation: OUS Extension Facts No., published by Oklahoma State University. 2752, Chemical Weed Management of Phosphorus Beans], Substituted ureas (I), as shown in several examples below, are superior to chloroxrone in both selectivity and soybean action for soybeans.

Ventazone has selectivity for soybeans, but also herbicides against grassy weeds (e.g. zombie, king's roe, ragweed, and some important leafy weeds (e.g., annual morning glory, hairy dandruff). [Weed management of soybeans published by the University of Tennessee Agricultural Extension Service (977)], as evident in the various examples presented below, substituted ureas (I), in addition to other important weeds, were found to Have strong herbicidal activity against ragweed, morning glory and hairy dandruff, so that the herbicide spectrum is clearly superior to ventazone The superior properties of substituted ureas (I) are evaluated when they are in a field state that is very similar to that of soybean fields. More remarkable.

The strong herbicidation and high selectivity of the soybean crops of substituted ureas (I) is due to the presence of a substitution in the right position of the benzene ring of a portion of phenethyl oxy and a portion of phenethyl oxy as shown in formula (I). Occurs.

The excellent properties of substituted ureas (I) are most pronounced with N'-4- [2- (4-methylphenyl) ethoxy] phenyl-N-methoxy-N-methyl urea.

The fact that substituted ureas (I) are superior to chloroxutone, a selective herbicide for soybeans currently used for both selectivity and / or herbicidal activity, and that substituted ureas (I) are ventazones over a large portion of their herbicidal spectrum. A much better fact makes it very useful for managing weeds in soybean fields. Substituted ureas (I) of the present invention are prepared in a number of ways, among which exemplary embodiments are described below.

Process A

Substituted urea (I) is a general formula

4-phenethyl oxyphenyl isocyanate salt (where X ₁ and X ₂ are as defined above) is an inert solvent (e.g., benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, N, O-dimethyl at a temperature of about -10 to 150 ° C. for about 10 minutes to 10 hours with or without chloroform, carbon tetrachloride, ethyl vinegar, pyridine, dimethyl formamide, water, or mixtures thereof). Prepared by reaction with hydroxyl amine.

Process B

Substituted urea (I) is of the general formula:

N '-(4-phenethyl oxyphenyl) -N-hydroxy urea (where X ₁ and X ₂ are as defined above, respectively) in a methylating agent (e.g., methyl oxide, methyl embrittlement, methyl sulfate , With or without an inert solvent (e.g., benzene, toluene, xylene, xylene, methanol, ethanol, isopropanol, diethyl ether, tetrahydrofuran, dioxane or mixtures thereof) with diazomethyl) Prepared by methylation at a temperature of 10 to 150 ° C. for about 0.5 to 10 hours in the presence of a base (eg sodium hydroxide, potassium hydroxide) if necessary.

Process C

Substituted urea (I) is of the general formula:

4-phenethyl oxyphenyl carbamyl chloride (where X ₁ and X ₂ are as defined above respectively) in an inert solvent (e.g., benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane Dechlorination agents (e.g., pyridine, triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate), if necessary, with or without chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethyl formamide or mixtures thereof. Prepared by reaction with N, O-dimethyl hydroxylamine at a temperature of about 0 to 150 ° C. for about 0.5 to 10 hours in the presence of

Process D

Substituted urea (I) is of the general formula

4-phenethyl oxyaniline (where X ₁ and X ₂ are each as defined above) is used as an inert solvent (e.g., benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform About 0.5 in the presence of a dehydrogenating agent (e.g., pyridine, triethylamine, sodium hydroxide), if necessary, with or without carbon tetrachloride, ethyl acetate, pyridine, dimethyl formamide or mixtures thereof. Prepared by reacting with N-methyl-N-methoxy carbamyl chloride at a temperature of about 0 to 150 [deg.] C. for 10 hours.

Process E

Substituted urea (I) is of the general formula

Halogenated phenethyl,

(Where X ₁ and X ₂ are each as defined above and Y is an atom of chlorine, cancellation or oxo). Inert solvents (e.g., benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate, methanol, ethanol, isopropanol, dimethyl formamido, Water or a mixture thereof), if necessary, in the presence of a dehydrogenating agent (e.g., pyridine, triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate) at a temperature of about -10 to 150 DEG C for about 0.5 to 10 hours. Is reacted with N '-(4-hydroxyphenyl) -N-methoxy-methyl urea at

The resulting substituted urea (I) is then purified, if necessary, in its usual process of recrystallization in a suitable solvent.

In the above-mentioned various processes, the starting material is known, or is manufactured by its own normal process.

For example, isocyanate phenethyl oxyphenyl (II) is conveniently prepared from the corresponding easily used nitro compound as shown below.

In the transplant, X ₁ and X ₂ are as defined above, respectively.

Table 1 shows examples of substituted urea (I) thus prepared.

TABLE 1

Practical, presently suitable forms for preparing substituted urea (I) are specified in the following examples.

Example 1 (Step A)

To a solution of 5.5 g of 4- (4-methylphenethyl oxy) isophenyl cyanate in 100 ml of benzene, a solution of 2 g of N, O-dimethyl hydroxyl amine in 50 ml of benzene was added dropwise at 20 to 30 ° C. Add. After the injection is completed, the reaction mixture is continuously stirred for 30 minutes at the same temperature.

The solvent was then removed under reduced pressure, and the residue was recrystallized from ethanol to give 7.4 g of N '-[4- (4-methyl phenethyloxy) phenyl] -N-methoxy-N-methyl urea as a white needle. Get

Melting Point: 82 ~ 83 ℃

Example 2 (Step B)

To a solution of 7 g of hydroxylamine hydrogen chloride and 4 g of sodium hydroxide in 15 ml of water in a solution of 4.7 g of 4- (2,4-dimethylphenethyl oxy) isocyanate in 50 ml of methylene chloride, temperature -20 It is added dropwise at ℃.

After dilution with water the precipitated crystals are filtered and dried to yield 4.3 g of N'-4- (2,4-dimethyl phenethyl oxy) phenyl-N-hydroxy urea.

To a solution of 4.3 g of hydroxyurea derivative in 200 ml of benzene-methanol (1: 1), 5 ml of 10N aqueous sodium hydroxide solution and 4 ml of dimethyl sulfate were added dropwise at a temperature of -30 ° C. After stirring to room temperature, the reaction mixture is diluted with water and extracted with benzene.

The solvent is removed under reduced pressure and the residue is recrystallized from ethanol to give 2.1 g of N '-[4- (2,4-dimethyl phenethyl oxy) -phenyl] -N-methoxy-methyl urea as a white needle. Melting Point: 95 ~ 95.5 ℃

Example 3 (Step C)

To a solution of 10.6 g of 4- (4-isopropyl phenethyloxy) phenylcarbamyl chloride in 200 ml of toluene, a solution of 2.5 g di N, O-methyl hydroxyl amine in 4 ml of pyridine and 50 ml of toluene- It is added at a temperature of 20 ℃.

The mixture is heated at reflux for 4 hours.

The reaction mixture is then poured into iced water, the separated organic layer is washed with dilute hydrochloric acid, washed thoroughly with water and dried over anhydrous sodium sulfate.

4.8 g of N '-[4- (4-isopropylphenethyloxy) phenyl] -N-methoxy-N-methyl urea, which was removed under reduced pressure, and the crude crystals were recrystallized from ethanol to give a white needle. Get Melting Point: 81 ~ 82 ℃

Example 4 (Step D)

A mixture of 26.9 g of 4- (4-tert-butyl phenyl oxy) aniline, 13 g of N-methoxy-N-methyl carbamyl chloride, 10 ml of pyridine and 300 ml of toluene is heated under reflux for 7 hours.

Water is then added to dissolve the pyridinium chloride, and the separated toluene layer is washed with dilute hydrochloric acid, washed thoroughly with water and dried over anhydrous sodium sulfate. This solvent was then removed under reduced pressure, and the obtained crude crystal was recrystallized repeatedly from ethanol to give 9.3 g of N- [4- (4-tert-butyl phenethyloxy) phenyl] -N-methoxy- as a white needle. Obtain N-methyl urea. Melting Point: 14 ~ 15 ℃

Example 5 (Step E)

To a solution of 8.8 g of sodium ethoxide in 200 ml of N, N-dimethyl formamide is added 27 g of N '-(4-hydroxymethoxy methyl) -N-methoxy-N-urea.

To this mixture is added dropwise a solution of 27 g of 4-methoxy phenethyl emulsified substance in 100 ml of N, N-dimethylformamide.

The mixture is then gradually heated to 100 ° C., kept at the same temperature for 5 hours and then poured into ice water.

The precipitated crystals are filtered off, washed in this order with water, ethanol and ether to dry the air.

This product is reconstituted in ethanol to give 11.8 g of N '-[4- (4-methoxy phenethyl oxy) phenyl] -N-methoxy-N-methylurea as white needles. Melting Point: 100 ~ 101 ℃

Practical usage of the substituted urea (I) is used as it is, or in any of the shaped shapes such as wet powder, emulsified aggregate, particulate form, powder and the like.

In preparing such shaped shapes, a solid or liquid carrier is used.

For solid carriers, ore powders (e.g. kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum calcium carbonate, apatite), plant powders (e.g., soy flour, flour, wood flour, Tobacco powder, starch, crystals, cellulose), high molecular compounds (e.g., petroleum resin, polyvinyl chloride, damat gum, ketone resin), alumina, wax and the like are produced.

As for the liquid carrier, alcohols (for example, methyl alcohol, ethyl alcohol, ethylene glycol, benzyl alcohol), ie hydrocarbons (for example, toluene, benzene, xylene, methyl naphthalene), halogenated hydrocarbons (for example, , Chloroform, tetrachloride, monochlorobenzene, ethers (e.g. dioxane, tetrahydrofuran), ketones (e.g. acetone, methyl, ethyl ketone, cyclohexanone), esters (e.g. For example, vinegar acid (ethyl, butyl acetate acetate, ethylene glycol acetate, acid amides (for example, dimethylformamide), nitriles (for example, acetonitrile), ether alcohols (for example, Ethylene glycol ethyl ether), water and the like.

Surfactants used for emulsifying, dispersing, and entraining can be any of the nonionic, anionic, cation and zwitterionic forms of the active agent.

Examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkyl arylethers, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, oxyethylene, polymers, acid polyoxyethylene alkyls, fatty acid salts, Alkyl sulfates, alkyl sulfonates, alkylaryl sulfur oxides, alkyl phosphates, polyoxy ethylenealkyl sulfates, quaternary ammonium salts, oxy alkylimines and the like.

However, the surfactant is of course not limited to these compounds.

If necessary, gelatin, casein, sodium alkate, starch agar, polyvinyl alcohol and the like can be used as a supplement.

Various practical forms of herbicidal compositions according to the invention are clearly shown in the following examples, in which parts and percentages are by weight.

Compound numbers correspond to those listed in Table 1.

[Formulation Example 1]

Compound no. 80 parts of 1, 5 parts of surfactant (polyoxy ethylene alkyl aryl ether type), and 15 parts of hydrated synthetic silicon dioxide are mixed well and milled simultaneously to obtain wet powder molding.

[Formulation Example 2]

Compound no. 30 parts of 4, 7 parts of surfactant (polyoxyethylene alkylaryl ether type), 3 parts of sodium alkyl arylsulfonate and 60 parts of xylene are mixed well to obtain a blend of emulsifying condensate.

Formulation Example 3

Compound no. 1 part of 3, 1 part of white carbon, 5 parts of sodium lignosulfonate, and 93 parts of clay are mixed well and milled simultaneously.

This mixture is then kneaded well, granulated and dried to obtain a granular blend.

[Formulation Example 4]

40 parts of bentonite, 5 parts of sodium lignosulfonate and 55 parts of clay are mixed and milled.

The mixture is then kneaded well with water, granulated and dried to give a granule free of active ingredient.

95 parts of these granular compounds showed compound No. 5 parts of 2 are added by immersion to give a granular formulation.

Compound no. 3 parts of 6, 0.5 parts of isopropyl phosphate, 66.5 parts of clay and 3 parts of talc are mixed well and milled simultaneously to obtain a powder blend. Substituted ureas (I) can be used in combination with other herbicides to enhance their action as herbicides. In some cases, synergism is expected.

Other herbicides include phenoxy herbicides such as 2,4-dichlorophenoxy acetic acid, 2-methyl-4-chlorophenoxy acetic acid, and 2,4-dichloro phenoxy acetic acid (including its esters and salts). : 2,4-dichlorophenyl-4'-nitrophenyl ether, 2,4,6-trichlorophenyl-4'-nitrophenyl ether, 2,4-dichlorophenyl-4'-nitro-3'-meth Diphenylether herbicides such as oxy phenylether and 2,4-dichloro phenyl-3'-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-4,6-bisethylamino-1,3,5 Triazine, 2-chloro-4-ethylamino-6-isopropyl amino-1,3,5-triazine, 2-methylthio-4,6-bisethyl amino-1,3,5-litazine and Triazine herbicides such as 2-methylthio-4,6-bisisopropyl amino-1,3,5-triazine, 4-amino-6-third-butyl-3-methylthio-1,2,4-tri Triazinone herbicides such as azine-5 (4H) -source, N '-(3,4-chlorophenyl) -N, N-dimethyl urea, N'-(3,4-deck) Rophenyl-N-methoxy-N-methyl urea, N '-(3-chloro-4-difluorochloromethylthiophenyl) -N, N-dimethyl urea, N'-4- (4-chlorophenoxy Substituted urease herbicides such as phenyl-N, N-dimethyl urea and N '-(a, a, a-trifluoro-M-tolyl) -N, N-dimethyl urea, isopropyl-N- (3 Carbamic acid herbicides such as -chlorophenyl) carbamate, methyl-N- (3,4-dichlorophenyl carbamate and 4-chloro-2-butynyl-m-chlorocarbanilate, S- (4- Fiolcarbamic acid herbicides such as chlorobenzyl) -N, N-diethylthiocarbamate, S-ethyl-N, N-hexa methylenethiol carbamate, S-ethyl-dipropyl thiolcarbamic acid salt, 3 , 4-dichloropropionanilide, N-methoxy methyl-2,6-diethyl-2-chloro acetanilide, and 2-chloro-2 ', 6'-diethyl-N- (butoxy methyl) acet anilide Acid anilide herbicides, such as 5-bromo-3-agent2-butyl-6-methyl uracil, and 3-shi Uracil herbicides such as clohexyl-5,6-trimethylene uracil, pyridinium salt herbicides such as 1,1'-dimethyl-4,4'-bispyridinium dichloride, N- (phosphono methyl) glycine, 0- Ethyl-0- (2-nitro-5-methyl phenyl) -N-second 2-butyl phosphoro amido thioate and 0-methyl-0- (2-nitro-4-methyl phenyl) -N-isopropyl Organo-phosphorus herbicides such as phosphoro amido thioate, a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine and N- (cyclopropyl methyl) toluidine herbicides, such as -a, a, a-trifluoro-2,6-dinitro-N-propyl-p-toluidine, N-second 2-butyl-4-third butyl-2,6-dinitroaniline , 3,5-dinitro-N, N-dipropyl-sulfanyl amide, 5-ze3-butyl-3- (2,4-dichloro-5-isopropoxy phenyl) -1,3,4- Oxa diazolin-2-one, 3-isopropyl-1H-2,1,3-benzothiadiazine- (4) -3H-one-2,2-2 oxide (including salts thereof), α- (β-naproxy) propy On anilide, 2- (α-naphthoxy) -N, N-diethyl propionamide, 3-amino-2,5-dichloro benzoic acid, 2-butyl-4,6-dinitrophenol, N-1- Naphthyl phthalamic acid, 2- (1-allyl oxy amino) butylidene-5,5-dimethyl-4-methoxy carbonyl cyclohexane-1,3-dione (including their salts), and the like. Is generated.

However, herbicides are, of course, not limited to these examples.

The herbicides of the present invention can be used in combination with fungicides, microbial insecticides, pesticidal insecticides, other and sexual insecticides, plant growth regulators or fertilizers. The concentration of substituted urea (I) as the active ingredient of the herbicidal compound is usually about 1 to 80% by weight, which is also used at higher or lower concentrations.

When using substituted urea (I) as herbicide, the method of use and the dosage rate depend on the formulation of the active ingredient, distillation of the crops grown, the type of weeds removed, climatic conditions, and the like.

As appropriate, it is used for both weeds and crop plants above the standard after emergency measures, but can be used at any time from the stage immediately after sowing.

The dosage is generally about 2 to 80 grams of active ingredient, suitably 5 to 40 grams, for the ares.

For example, the use on arable land is carried out at a dose of about 2 to 80 grams to the malt by top-leaf treatment on weeds of about 1 to 15 cm in height. Also, for example, the use in rice fields is carried out by administration of the active ingredient in an amount of about 2 to 80 grams to the malt until watering within 4 weeks after seeding of the seedlings.

The following several examples illustrate some representative test data showing excellent herbicidal activity of the compound (I) of the present invention.

Compound numbers correspond to those listed in Table 1.

Example 1

Herbicides and Selectivity of Soybean of Compound [I] of the Present Invention by Application to Leaves

Fill the plastic bowls (35 × 25 × 10 cm) with upland soil, and sowing soybeans, skewers, radishes, whisk amaranths, white oysters, bitter hawks, annual morning glory, squids, king blues and blood seeds in each bowl Allowed to grow for two weeks.

A projected dose of test compound was sprayed onto the leaves at the top of the test plant with a small manual nebulizer.

When using the compound, the beans were in the whisper stage, the heights of the hawks, radishes, hairy squirrel, white hawk, hawk hawk and annual morning glory were 2-6 cm, and 4-10 cm of zombies, king cots and blood. After spraying, the test plants were placed in the greenhouse for three weeks and the herbicidal action was evaluated as follows.

The aerial portion of the test plant is cut and weighed (new weight), calculated as the new weight of the untreated plant, which is 100% of the weight of the untreated plant to the weight of the untreated plant, and the crop The damage and herbicidal activity of were evaluated by the criteria shown in the table below.

The results are shown in Table 2.

In use on the leaves described above, the projected amount of the test compound was molded to an emulsifying concentration, dispersed in water containing a humectant, and sprayed at a volume of 3 liters per arc.

TABLE 2

Note: * Described in Swiss Patent 532,891.

Example 2

Herbicidal action and crop selectivity of the compound (I) of the present invention by use on leaves:

Fill the highland soils at Wagner's pots (1/5000 are), and in each pot, beans, peanuts, corn, rice, lizards, crows, sunflowers, annual morning glory, gomans, hairy scabbards, persimmons, tortoises, and doggrass And seed of king burrow.

As the test plants grew to the stages shown in Table 3, the desired amount of test compound was sprayed onto the leaves at the top of the test plants with a small hand sprayer.

After spraying, the test plants were allowed to grow for 4 more weeks, and the damage to the crop plants and the herbicidal action against the weeds were evaluated according to the criteria shown in Example (I). The results are shown in Table 3.

By use on the leaves described above, the projected amount of the test compound was shaped into an emulsified condensate, dispersed in water containing a humectant and sprayed at a volume of 3 liters per malt.

The growth stages of each test plant in use are shown in Table 3.

TABLE 3

Example 3

Herbicidal Activity and Crop Selectivity of Inventive Compound (I) by Soil Use:

Several pots (1/5000 are) of Wagner were filled with high-altitude soil, and seeds of soybeans, cotton, maize, wheat, hair agar, white malt, radish, chickweed and squid were sown in different pots.

The projected amount of the test compound molded into the wet powder was dispersed in water and sprayed into the soil plane with a small manual sprayer at a volume of 3 liters per malar.

After spraying, the test plants were placed in the greenhouse for 3 weeks to assess crop damage and herbicide action.

This evaluation was performed according to the criteria shown in Example (I).

The results are shown in Table 4.

TABLE 4

Example 4

Herbicidal action and selectivity of the compound (I) of the present invention on rice under the condition of rice:

Wagner's pot (1/5000 are) was filled with paddy field soil (1.5 kg bowl) and preserved under flood conditions. Seeds of rice, which are three-leaf stages, were transferred to this, and seeded with blood seeds, and grown for 5 days.

A planned amount of test compound was then used for the aqueous layer. In 25 days of use, herbicides and crop damages were assessed on cultivated rice crops and blood, as well as naturally occurring almonds and broad-leaved weeds (e.g., stilts, perillas, and flowers).

The results are shown in Table 5.

Herbicidal action and crop damage were evaluated according to the criteria shown in Example (I).

To use the test compound, a predetermined amount thereof was molded into a wet powder, diluted with water, and used in an aqueous layer at a rate of 15 ml for each bowl with pipette.

TABLE 5

Example 5

In Field Studies on the Herbicidal Activity and Selectivity of Soybean of Compound (I) of the Present Invention with the Use of Leaves

Seeds of beans, sunflowers, macaws, scion, annual morning glory datura, yam, hair amaranth and goman were simultaneously sown in each region (2 m2 per earth, three identical shapes) under the condition of highland fields.

When the soybean crop was grown in the fourth trilobal phase, the desired amount of test compound was sprayed onto the leaves at the top of all the test plants with a manual sprayer.

After spraying, the test plants were allowed to grow for 16 more days and the damage and herbicidal activity of the crops were evaluated as follows. The aerial portions of the test plants were cut and weighed (new weight).

The percentage of the new weight of the treated plant to the weight of the untreated plant was calculated as 100 of the untreated new weight.

The results are shown in Table 6.

In use on the leaves described above, the projected amount of the test compound was molded into wet powder, dispersed in water containing the wetting agent and sprayed at a volume of 3 liters.

The growth stages of each test plant at the time of use are described in Table 6.

TABLE 6

Claims (1)

Next Structural Formula (II)

Of 4-phenethyl oxyphenyl isocyanate with N, O-dimethyl hydroxyl amine to give the following structural formula (I)

Production method of N '-[4- (substituted phenethyloxy) phenyl] -N-methyl-N-methoxy urea obtained. [Wherein X ₁ is a hydrogen atom or a methyl group, X ₂ is a C ₁ to C ₅ alkyl group such as methyl, ethyl, propyl, butyl, pentyl or a C ₁ to C ₅ alkoxy group (eg methoxy, Methoxy, propoxy, butoxy, pentoxy)]