CS228913B2 - Herbicide and method of preparing active substances thereof - Google Patents

Abstract

NEW MATERIAL:A substituted phenylsulfonylurea derivative expressed by forformulaI[X is phenyl or phenoxy; R is formula II (R1 and R2 are methyl or methoxyl) or formula III]. EXAMPLE:N-2-Biphenylylsulfonyl-N'-(4-methoxy-6-methyl-pyrimidin-2-yl)u rea. expressed by formula IV. USE:A herbicide capable of exhibiting an accurate and selective herbicedal effect in a small amount of a chemical without giving the phytotoxicity, particularly exhibiting a remarkable controlling effect in use as a soil treating agent or foliar and soil treating agent in weeds in paddy fields, and having improved safety and a wide herbicidal spectrum. PROCESS:A compound expressed by formula V is reacted with a compound expressed by the formula NH2-R to give the aimed compound expressed by formulaI.

Description

The present invention provides novel substituted phenylsulfonylureas, processes for their preparation, and herbicidal compositions containing these derivatives as active ingredients.

The novel substituted phenylsulfonylureas according to the invention correspond to the general formula I

in which

X is phenyl or phenoxy and

R is a radical of formula

CHj kde

R 1 and R ² are methyl or methoxy.

The substituted phenylsulfonylureas of formula (I) may be prepared as described below, which is also within the scope of the invention. Accordingly, the present invention also provides a process for the preparation of substituted phenylurea derivatives of formula (I) above, characterized in that the compound of formula (II)

SOgN x un

or in which

X is as defined above,

is reacted with a compound of formula III

NH2 — R, (ΠΙ) in which

R is as defined above.

The invention furthermore relates to a herbicidal composition comprising, as active substances, substituted phenylsulphonylurea derivatives of the aforementioned general formula (I).

U.S. Patent Nos. 4,127,405 and 4,169,719, as well as Japanese Patent Application Publication No. 52-122,384, disclose that compounds of Formula IV

W

R1-SO2-NH-C-NH-R, (IV) wherein

R is a radical of formula

or

R 1 is a radical of formula

R ₆

or

R 3 and R 6 are each independently hydrogen, fluorine, bromine or iodine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, trifluoromethyl, cyano, CH 3 S (O) _n - or CH 3 CH 2 S (O) _n _

R a represents a hydrogen, fluorine, chlorine or bromine atom or a methyl group,

R 5 represents a hydrogen, fluorine, chlorine or bromine atom, a methyl group or a methoxy group,

R7 is hydrogen, fluorine or bromine, alkyl having 1 or 2 carbon atoms or alkoxy having 1 or 2 carbon atoms,

R 5 represents a hydrogen atom, a methyl group, a chlorine or bromine atom,

R9 and R10 are each independently hydrogen, methyl, chlorine or bromine,

W and Q independently represent oxygen or sulfur, n is 0, 1 or 2,

X is hydrogen, chlorine or bromine, methyl, ethyl, C 1 -C 3 alkoxy, trifluoromethyl, CH 3 S- or CH 3 OCH 2 -, and

Z represents a methyl group or a methoxy group, with the proviso that

(a) if R5 is not hydrogen, at least one of R3, R4, R6 and R7 must be other than hydrogen and at least two of R3, R4, R6 and R7 must be hydrogen,

(b) when R5 is hydrogen and all R3, R4, R6 and R7 are different from hydrogen, then all R3, R4, R6 and R7 must be either chlorine or methyl; and

(c) when both R 3 and R 7 are hydrogen, at least one of R 3, R 4, R 5 and R 6 must be hydrogen, and their agriculturally safe salts show a herbicidal action.

As a result of extensive studies of substituted phenylsulfonylurea derivatives in an attempt to find new types of these derivatives having a better herbicidal effect, it has now been found that the new substituted phenylsulfonylureas of the formula I exhibit an excellent selective herbicidal effect which has not been possible formula IV to expect.

In other words, in comparison to conventional herbicides which, despite their herbicidal activity even at relatively low doses, are highly phytotoxic to rice plants, the substituted phenylsulfonylureas according to the invention are not phytotoxic at all and exhibit excellent selective herbicidal properties even at low doses. effect.

The compounds according to the invention show an excellent selective effect, in particular when used for soil pre-emergence treatment and for use in the treatment of plant stems and leaves, as well as in the treatment of soil in rice crops to control weeds. The compounds of the invention are superior in safety, have a better herbicidal effect than the compounds of known and broader spectrum of herbicidal activity. For example, the compounds described are characterized by acting as herbicides on the following weeds occurring in paddy fields without causing any damage to the rice plants:

Dicotyledonous weeds:

Rotala indica Koehne

Lindernia procumbens Philcox, Ludwigia prostrata Roxburgh, Potamogeton distimctus A. Benn., Elatine triandra Schk.

Monocotyledonous weeds:

Echinochloa crus-galli Beauv. var.,

Monochoria vaginalis Presl.

Eleocharis acicularis L.,

Eleocharis Kuroguwai Ohwi

Cyperus dlfformis L.,

Cyperus serotinus Rottboell,

Sagittaria pygmaea Miq.

Alisma canaliculatum A. Br. et Bouche, Scorpion juncoides Roxburgh var.

The compounds of the invention are further characterized in that they exhibit herbicidal activity against, for example, the following weeds occurring in the fields, without having any detrimental effect on the following useful plants:

Dicotyledonous weeds:

Polygonům sp. [rdesnoj,

Chemopodium album Linnaeus (White Goosefoot),

Stellaria media Villars (Common Chickweed,

Portulaca oleracea Linnaeus (Common Purslane).

Monocotyledonous weeds:

Echinochloa crus-galli Beauv. var. (hedgehog corns the leg),

Digiiaria adscendens - Henr. Cyperus iria L. (flatsedge).

Utility plants:

dicotyledons such as mustard, cotton, carrots, peas and beans artichokes, potatoes, beets, etc., monocotyledons such as corn, rice, oats, barley, wheat, millet, sugar cane, etc.

However, the abovementioned plant names are to be regarded only as representative of genera designated by Latin names. However, the applicability of the active compounds according to the invention is in no way limited to weeds in rice and common fields. These compounds are also effective against weeds occurring in rushes, against weeds on eels and the like. The term "screens", in the broadest sense, includes all plants growing in places where they are undesirable.

The substituted phenylsulfonylureas of the above general formula I according to the invention are prepared according to the following reaction scheme:

In the formulas shown in this scheme, X and R are as defined above. Special - examples for the symbol X include phenyl 'and phenoxy, special ´ examples for the symbol R then

4,6-dimethylpyrimidin-2-yl,

4,6-di.methoxypyriidin-2-yl,

4-im ^, 4-thoxy-6-a-4-ylpyrimidin-2-yl,

4,6-dimethyl-1,3,5-triazin-2-yl,

4,6-dimethoxy-1,3,5-triazin-2-yl, 4-methoxy-6-methyl-1,3,5-triazin-2-yl and the like. In the process for the preparation of the compounds of the formula I shown in the above reaction scheme, particularly suitable starting materials, i.e. compounds of the formula II, are particularly suitable.

2-biphenylsulfonyl isocyanate and 2-phenoxyphenylsulfonyl isocyanate.

The intermediates of formula (II) above are not yet known. These may be prepared in a manner not within the scope of the present invention

by the phenylsulfonamides of the general formula V

SOíNHi

VI {VI in which

X as above is phenyl or phenoxy, reacted in the presence of an aliphatic isocyanate and optionally in the presence of a diluent with phosgene (COCl 2) or trichloromethyl chloroformate (CClO-CO-C1).

If 2-phenoxyphenylsulfonamide and phenylene are used as starting materials, and n-butyl isocyanate is used as the aliphatic isocyanate, the reaction may be described as follows:

-2HCI

It is necessary to carry out this reaction in the presence of an aliphatic isocyanate which can be regenerated and reused after the reaction is complete. Alkyl isocyanates having from 3 to 8 carbon atoms or cycloalkyl isocyanates having from 5 to 8 carbon atoms are preferably used. Examples of such isocyanates are n-butyl isocyanate, n-hexyl isocyanate and cyclohexyl isocyanate.

Suitable diluents for working in the manner described above are all customary inert solvents, for example hydrocarbons such as hexane, cyclohexane, petroleum ether, ligroin, toluene, xylene, chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene or chlorobenzene, ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane or tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, methylisopropyl ketone or methyl isobutyl ketone, nitriles such as acetoniiril or propionitrile, esters such as ethyl ester or amyl esters such as dimethylformamide or dimethylacetamide, sulfones and sulfoxides such as sulfolane and dimethyl sulfoxide, and bases such as pyridine.

It is preferred to carry out the reaction (V) - + (11) in the presence of a suitable catalyst. Particularly suitable catalysts are tertiary amines such as triethylamine, dimethylcyclohexylamine and 1,4-diazabicyclo [2.2.2] octane.

The reaction temperatures of reaction (V) -> (11) can be varied within wide limits. In general, the reaction is carried out at a temperature between -20 ° C and the boiling point of the reaction mixture, preferably between 80 and 150 ° C. The reaction is usually carried out at normal pressure, but can also be carried out at elevated or reduced pressure.

In reaction (V) -> (11), 1 to 2 moles, preferably 1.05 to 1.3 moles of aliphatic isocyanate and 1 to 4 moles, preferably 1 to 1.5 moles are generally used per mole of phenylsulfonamide of formula (V). phosgene, and 0.5 to 1 mol, preferably 0.55 to 0.65 mol, of trichloromethyl chloroformate. The catalyst is used in an amount of 0.1 to 5 g, preferably 0.8 to 2.2 g, for each mole of the compound of formula V.

Treatment of the reaction mixture and isolation of the phenylsulfonyl isocyanate of formula 11 is carried out in a conventional manner. These isocyanates can be purified, for example, by distillation.

Reaction (V) - (11) is illustrated in greater detail in the following preparations.

Example 1 ' / y-SO2N2 & O

A mixture of 23.3 g of 2-biphenylylsulfonamide, 10.9 grams of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo [2.2.2] octane and 150 ml of xylene is heated to reflux for 1 hour with stirring. The solution was added dropwise over 2.5 hours while maintaining the temperature at 120-125 ° C

11.9 g of trichloromethyl chloroformate in 30 ml of xylene. After the addition was complete, the above temperature was maintained for some time, then the mixture was heated to reflux for a short time to complete the reaction. After completion of the reaction, xylene and n-butyl isocyanate are distilled off under reduced pressure. 22.0 g of highly pure 2-biftnylyl-sulfonyl-isocyanate having a boiling point of 135 DEG-137 DEG C./93 mmHg are obtained.

Preparation 2

A mixture of 25.0 g of 2-phenoxyphenylsulfonamide, 14.0 g of n-hexyl isocyanate, a catalytic amount of 1,4-diazabicyclo [2.2.2] octane and 150 ml of xylene is stirred and heated to reflux for 1 hour. as in Preparation 1, was reacted with a solution of 11.9 g of trichloromethyl chloroformate in 30 ml of xylene. After completion of the reaction, xylene and n-hexyl isocyanate are distilled off to give 22.8 g of the desired 2-phenoxyphenylsulfonyl isocyanate, b.p. 146-150 ° C / 0 mm Hg.

Preparation 3

A mixture of 23.3 g of 2-biphenylylsulfonamide, 10.9 g of n-butyl isocyanate, a catalytic amount of 1,4-diazabicyclo [2.2.2] octane and 180 ml of chlorobenzene is stirred and heated to reflux for 2 hours. a slight excess of phosgene over the theoretical amount is introduced into it over 2 hours, maintaining the temperature of 115-120 ° C. If unreacted phosgene leaves the reaction system during this time, it is trapped in a solid carbon dioxide freezer and returned to the reaction vessel. After the phosgene was introduced, the reaction mixture was stirred under reflux for a short period of time to complete the reaction, then cooled, if necessary, to remove insolubles by filtration under reduced pressure, and the filtrate was evaporated under reduced pressure. There were obtained 20.0 g of the desired 2-bifenylylsulfonylisokyanátu b.p. 135-137 ⁰ C / 93 to 106 mbar.

Specific examples of other starting materials, i.e. compounds of formula III, are given

2-amino-4,6-dimethylpyrimidine,

2-amino-4-methyl-6-methylpyrimidine,

2-amino-5-methoxy-6-methyl-1,3,5-triazine,

2-amino-4,6-dimethoxy-1,3,5-triazine and the like.

The reaction (II) 4- [III] -> (I) according to the invention can be illustrated in more detail by way of example illustrated by the following reaction scheme:

The processes for the preparation of the active compounds according to the invention are preferably carried out in the presence of a solvent or diluent. Any inert solvent or diluent may be used for this purpose. Examples of such solvents or diluents include aliphatic, alicyclic and aromatic hydrocarbons (which may optionally be chlorinated), such as hexane, cyclohexane, petroleum ether, petroleum, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene, chlorobenzene and the like. ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, propylemoxide, dioxane, tetrahydrofuran and the like; ketones such as acetone, methyl ethyl ketone, methylisopropyl ketone, methyl isobutyl ketone and the like; nitriles such as acetonitrile, propionitrile amyl acetate and the like, acid amides such as dimethylformamide, dimethylacetamide and the like, sulfones, sulfoxides and the like, such as dimethyl sulfoxide, sulfolane and the like, and bases such as pyridine and the like.

The process according to the invention can be efficiently introduced in the presence of a catalyst, for example 1,4-diazabicyclo [2.2.2] octane and the like.

The process according to the invention can be carried out over a wide temperature range. In general, the reaction is carried out at a temperature between -20 ° C and the boiling point of the reaction mixture, preferably between 0 ° C and 100 ° C. The reaction is preferably carried out at normal pressure, although it is also possible to work at elevated or reduced pressure.

When the compounds of the invention are used as herbicides, they can be used as such after simple dilution with water, or in the form of a variety of agrochemical preparations which are produced using agricultural auxiliaries by conventional methods of producing agrochemicals.

These preparations of various kinds can be used as such in practice or can be diluted with water as desired

2-8.913 concentration. The term "agricultural auxiliaries" as used herein includes, for example, diluents (solvents, fillers and carriers), surfactants (solubilizers, emulsifiers, dispersants, adhesives, aerosol propellants, synergistic additives, etc.).

Examples of suitable solvents include water as well as organic solvents, for example hydrocarbons [such as n-hexane, petroleum ether, naphtha, petroleum fractions (paraffin wax, kerosene, gas oil, medium oil, heavy oil, etc.), benzene, toluene, xylene, etc.], chlorinated hydrocarbons (such as methylene chloride, carbon tetrachloride, trichlorethylene, ethylene chloride, ethylene dibromide, chlorobenzene, chloroform and the like), alcohols (such as methanol, ethanol, propyl alcohol, ethylene glycol, etc.), ethers (such as ethyl ether, ethylene oxide, and the like), ether alcohols (such as ethylene glycol monomethyl ether, etc.), ketones (such as acetone, isophorone, etc.), esters (such as ethyl acetate, amylacetate, etc.), amides (such as dimethylformamide, dimethylacetamide, etc.), sulfoxides (such as dimethylsulfoxide and the like). etc.

Examples of fillers or carriers are inorganic powdered solids such as sulfur, slaked lime, magnesium lime, gypsum, calcium carbonate, diatomaceous earth, perlite, pumice, calcite, diatomite, amorphous silica, alumina, zeolite, mineral clays (e.g. pyrophyllite) , talc, montmorillonite, beidellite, vermiculite, kaolinite, mica, etc.), vegetable solid powders such as cereal flour, starch, starch, sugar, glucose, comminuted vegetable stems, etc., powdered materials consisting of synthetic resins, for example phenolic resins, urea resins, vinyl chloride resins, etc.

Examples of surfactants include anionic surfactants. such as alkyl sulfates (e.g. sodium lauryl sulfate), arylsulfonic acids (e.g. alkylarylsulfonate, sodium alkylnaphthalenesulfonate and the like), succinic acid salts, sulfuric acid ester salts with polyethylene glycol-alkyl aryl ethers, and the like, cationic surfactants such as alkylamines (e.g. , polyoxyethylenalkylamines and the like, nonionic surfactants such as polyoxyethylene glycol ethers (e.g. polyoxyethylene-alkylarylether and condensation products thereof, etc.), 1 ' trers (e.g. polyoxyethylene fatty acid esters, and the like), polyol esters (e.g. polyoxyethylene sorbitan). and the like), ampholytic surfactants and the like.

Examples of other excipients are stabilizers, adhesives (e.g., agricultural soaps, casein lime, sodium alginate, polyvinyl alcohol, vinyl acetate-based adhesives, acrylic adhesives, etc.), delaying agents, dispersion stabilizers (e.g. casein, tragacanth, carboxymethylcellulose, polyvinyl alcohol, etc.), synergistic additives, etc.

The compounds of the present invention can be formulated into active formulations of various types by conventional methods for producing agrochemical formulations. Examples of the above preparations are emulsions, oily solutions, wettable powders, aqueous solutions, suspensions, powders, granules, powder mixtures, capsules and the like.

The herbicidal compositions according to the invention may contain the abovementioned active ingredients in an amount of from 0.001 to 100% by weight, preferably from 0.05 to 95% by weight.

The herbicidal compositions according to the invention may contain the abovementioned active compounds in an amount of from 0.001 to 100% by weight, preferably from 0.05 to 95% by weight. _r

In practice, the active compound content of the compositions of the invention is generally from 0.01 to 95% by weight, preferably from 0.05 to 60% by weight. The content of active ingredient in the applied preparation may vary depending on the type of preparation, the method of application, the purpose, time and place of application, the degree of weed infestation and the like.

If desired, the compounds of the invention may be used in combination with other agrochemicals such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators as well as soil conditioners [e.g., organic phosphates, carbamate derivatives, organic chlorine derivatives, dinitroderivatives, organic sulfur compounds or organometallic compounds, antibiotics, substituted diphenyl ethers, urea derivatives, triazine derivatives and the like], or / and fertilized aipod.

In particular, by adding a suitable amount of additional active ingredient to the compound of the invention, it is possible to achieve a broadening of the spectrum of herbicidal activity and a more certain effect, while a synergistic effect is also expected. Examples of such other active substances are:

2-chloro-2 ', 6'-diethyl-N- (butoxymethyl) acetanilide,

N- (O, O-dipropyl-diethylphosphorylacetyl) h-11-di-eridine,

S- ((^ - Β ^^^ γΙ ^^ θι ^ ζυΙΙ - N, N-diethylthiol)

-carbamate,

O-methyl-O- (2-nitro-p-tolyl) -N-isopropylphosphoramide thirate,

O-ethyl-O- (2-nitro-5-methylphenyl) -N-sec-butylphosphoramide thioate,

3,4-dimethyl-2,6-dinitro-N-1-ethyl-propyl-anilide, α, α, α-α-η 4 -fluoro-2,6 - (η 4 -nitro-N, N-dipropyl-p-ioluidine,

2-chloro-2 ‘, 6‘-diethyl 1-N- (n-propoxy ethyl) acetanilide,

4.5- dichloro-34hiazol-2-yloxy-acetyl-N-isopropyl-N-ethoxyethoxyamid, e-l-ethyl ^^ - thiadiozol-ylolyxcac tlΓ-2 ^', 3', 4'ltetrahyciroи: hinolid,

Benzothiazol-2-yloxyacetic acid N, N-diallylamine,

Benzoxazole-2-oxy-oxoic acid N-sec / butyl-N-methylamide,

Benzoxazol-2-yloxyacetic acid N-cyclohexyl-N-methylamide,

Benzothiazol-2-yloxyacetic acid N-methyl-N- (1-methylpropargyl jamide),

^{N-benzyl-N-prop:} rgylamid benzoxazol-2-yloxyociové acid

2‘-Methylpiperidine-benzothiazol-2-yloxyacetic acid

2'l4 ^t -dimeteylpiperidtd benzoteiazoll -2-yloxyacetic acid,

Benzoxazol-2-yloxyacetic acid, 2‘4‘16‘‘trimethyl-piperidide, benzamazol-2-yloxyacetic acid, hexamethylenimide, benzo-2-yloxyacetic acid, benzothiazole-2-yloxyacetic acid perhydroindolidide, benzoxazol-2-yloxyacetic acid perhydride,

Benzothiazol-2-yloxyacetic acid Γ, 2‘13 ‘, 4‘-teiraeydrocemolide,

Benzoxazol-2-yloxyacetic acid, 2‘-methyl-12‘‘‘‘llletet,

N-> 611 → 3: 011 ^ benzoxazol-2-yloxyacetic acid,

Benzothiazol-2-yloxyacetic acid N-methylanilide,

Benzoxazol-2-yloxyacetic acid N-ethylanilide,

Benzoxazol-2-yloxyacetic acid N-propylanilide,

Benzoxazo-2,4-yloxyacetic acid N-isopropylanilide,

N-methyl-N-2‘-methoxyaniltd benzothiazole-2-oxy-acetic acid,

Benzoxazole-2lyl-oxyocioic acid, NlmethyllN122-methoxyanilide,

Nlme-ethyl-N12'ltrifluo ^! benzoxazole-2lyloxyacetic acid r-eylamide,

Benzothiazol-2-yloxyacetic acid, N-meteyl-N12‘-celoгganШd,

N-methyl-N-2 ^<-celoramltd benzoxazol-2-yloxyacetic acid,

Benzothiazol-2-yloxyacetic acid, N-methyl-N-2-fluoroanilide,

N-methyl-N-2 ^{<lfluoranilid} benzoxazole ^ -yloxyoctové acid

N-meihyl-N-3 ^{<-meteylamlid} benzothia'zol-2-yloxyacetic acid,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3-methylmethylanidide,

Benzothiazol-2-llyloxyacetic acid N-methyl-11'-methoxyanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3'-methoxy-amide,

Benzothiazol-2-yloxyacetic acid N-methyl-N-3‘-isopropoxyanilide,

Benzoxazol-2-yloxyacetic acid N-meteyl-N-3‘-isopropoxyanilide,

N-methyl-N-3‘-trifluoromethyl-alanilide of benzoisole-2lyloxyacetic acid,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3 3-rifluoromethylanilide,

N-methyl-N-3‘-chloroamido-benzothiazol-2-yloxyacetic acid,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3‘-chloramide,

Benzothiazole-2-llyloxyacetic acid N-methyl-N-3‘-fluoroanthide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3‘-fluoroanilide,

Benzothiazol-2-yloxyacetic acid N-methyl-N-3‘-bromoanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3'-bromoanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-4‘-methylanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-4‘-methoxyanilide,

N-methyl-N-4‘-fluoroanilide-benzoxazol-2-yloxyacetic acid,

Benzoxazol-2-yloxyacetic acid N-methyl-N-2 ', 3'-dimethylamide,

Benzoxazol-2-yloxyacetic acid N4-methyl-N-2 ‘, 3‘-dichloroanilide,

Benzothiazol-2-yloxyacetic acid N-methyl-N-2 ', 3'-dichloroanilide,

Benisoxazol-2-yloxyacetic acid N-methyl-N-4‘-chloro-2‘-methylanilide,

Benzoxazol-2-yloxy-acetic acid N-methyl-N-2 ', 5'-dichloroanilide,

Benzothiazol-2-yloxyacetic acid N-methyl-N-3 ‘, 5‘-dimethylanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3 ‘, 5‘-dimethylanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3 ', 5'-di-trifluoromethylanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-5‘-indanylamide,

Benzothiazol-2-yloxyacetic acid N-methyl-N-3‘-ethylanilide,

Benzoxazol-2-yloxyacetic acid N-methyl-N-3‘-ethylanilide,

Benzothiazo-2-yloxyacetic acid N-isopropylanilide and the like.

The compositions and directly applicable formulations containing the above-mentioned active compounds according to the invention can be applied by the methods generally used for agrochemical applications, for example by application of solutions, fogging, dusting, granulate tossing, water treatment, watering and the like. The described compositions can also be applied by the so-called ULV-postuip (Ultra-Low-Volume), in which the applied composition can consist of up to 100% of the active substance or substances. The dosage per unit area is about 0.1 to 3 kg / ha, preferably 0.2 to 1 kg / ha, based on the pure active ingredient. In special cases, however, it is possible or even necessary to use a dosage which is higher or lower than the above range.

Accordingly, the present invention also provides an herbicidal composition comprising the above compound of formula (I) and a diluent (solvent and / or filler and / or carrier) and / or a surfactant, and optionally, for example, a stabilizer, an adhesive and a synergist.

The invention also provides a method of controlling weeds, wherein a compound of formula I, either alone or in combination with a diluent (solvent or filler and / or carrier) and / or a surfactant and optionally, for example, a stabilizer, an adhesive and a synergist on weeds or their environment.

The following examples illustrate the compositions of the present invention, but do not limit the scope of the invention in any way.

Example 1

A wettable powder of parts of Compound No. 1 according to the invention, 80 parts of a mixture of diatomite powder and clay (1: 5), 2 parts of sodium alkylbenzene sulfonate and 3 parts of the condensation product of sodium alkylnaphthalene sulfonate and formalin are ground and mixed to form a wettable powder. This powder is diluted with water and sprayed onto the weeds and / or their environment.

Example 2

The emulsion of parts of Compound # 2 of the invention, 55 parts of xylene, 8 parts of polyoxyethylene-alkylphenyl ether and 7 parts of calcium alkyl-1-benzenesulfonate is mixed with stirring to form an emulsion which is diluted with water and applied to weeds and / or their environment.

Example 3

The dusts of Compound No. 3 according to the invention are ground and admixed with 98 parts of clay powder to form a powder composition which is applied by spraying on the weeds and / or their environment.

Example 4

Dust

1.5 parts of Compound No. 4 according to the invention,

0.5 parts of isopropyl hydrogen phosphate and 98 parts of powdered clay are ground and mixed to form a powdered composition which is applied by spraying on the weeds and / or their environment. Test performance

Example 5

Granulate

10 parts of compound 5 according to the invention, 30 parts of bentonite (montmorillonite, 58 parts of talc and 2 parts of lignin sulphonate) are mixed, 25 parts of water are added to the mixture and mixed thoroughly. 0.42 to 2.0 mm, which is dried at a temperature of 40 to 50 [deg.] C. The granules obtained are applied by spreading on the weeds and / or their environment.

Example 6

The granules of 0.2 to 2 mm mineral clay particles are introduced into a rotary mixer, uniformly wetted by spraying with a solution of 5 parts of compound 6 of the invention in an organic solvent and dried at 40 to 50 ° C. The granulate obtained is applied by spreading on the weeds or / or on their environment.

Compared to known active substances with analogous structure and activity, the novel compounds according to the invention are characterized in that they exhibit a considerably better effect and only a very low warm-blooded toxicity. Consequently, the compounds according to the invention are very valuable substances.

The outstanding advantages and significant efficacy of the compounds according to the invention are demonstrated by the results obtained in the following tests, in which the compounds according to the invention were introduced against various weeds.

Test 1

This test describes the treatment of stems and leaves as well as soil under irrigation conditions against water-growing weeds in crops. rice (bowl test).

Preparation of the preparation containing the active substance

The preparation containing the respective active ingredient is prepared by mixing the active ingredient (1 part by weight), 5 parts by weight of acetone as carrier and 1 part by weight of emulsifier to form an emulsion. The determined amount of this preparation is then diluted with water

The 2 dm2 Wagner dishes are filled with rice soil and seedlings are planted. rice (variety Kinmaze) in the stage of 2 to 3 leaves (plant height about 10 cm). Two seedlings are placed in each dish. The dishes are then inoculated with the seeds of Echinochloa crus-galli Beauv. Var., Cyperus iria L., Monochia vaginalis Presl., Sclrpus juncoides Roxburgh var. As well as broadleaf weed cuttings Eleocharis acicularis L. and Cyperus roots. serotinus Rottboell and Sagitta.ria pygmaea Miq. and the dishes are kept moist. After the hedgehog plants corn their feet [Echinochloa crus-galli Beauv. var.) to approximately 2-leaf stage (7-9 days after inoculation), the dishes are flooded with water (water column height about 6 cm) and a predetermined amount of each of the test compounds of the invention in the form of an emulsion is dropped. During the 2 days after treatment, the water is again drawn at a rate of 2 to 3 cm of water column height per day, after which the water column height is maintained at about 3 cm in the trays. The herbicidal effect and the degree of phytotoxicity were evaluated 4 weeks after the chemical treatment using the scale 0 to 5 below.

The evaluation of the effect is carried out on the basis of the degree of weed control compared to the status on the untreated area, using the following scale:

95% or more destruction

80% to 95% destruction

50% and 80% destruction

30% and 50% destruction

10% and 30% destruction less than 10% destruction (no effect)

Phytotoxicity for. The rice plants are evaluated taking into account the state of the plants in the untreated area using the following scale:

90% or more (destruction)

50% to 90. %

30% to 50%

10% to 30% less than 10% but not 0 0 0% (no phytotoxicity)

The results obtained are shown in Table 1 below:

Claims (2)

Herbicidal composition, characterized in that it contains at least one substituted phenylsulphonylurea of the formula I-N-SQ _and -NH-C-NH-R X Cl) in which X is phenyl or phenoxy and R represents a radical of formula ynAlezu where R @ ¹ and R @ ² are each methyl or methoxy. 1. Compound numbers correspond to those given in the following Examples and Table 2. 2. The symbols A, V, C, D, E, F, G and H indicate the following weeds: Echinochloa crus-galli Beauv. var. Eleocharis acicularis L. Cyperus iria L. D Scirpus juncoides Roxburgh var. E Monochoria vaginalis Presl. F broadleaf weeds (such as Lindernia procumbens Philcox, Rotala Indica Koehine, Elatine triandra Schk, etc.). G Cyperus serotinus Rottboell H Sagittaria pygmaea Miq. 3. Comparative substance IV-1 is N-2-chlorophenylsulfonyl-N - (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea corresponding to the formula O - ('У w Cl OCH, ύ (compound disclosed in Japanese Published Application 52-122 384). The following examples illustrate the preparation of the active compounds according to the invention. Example 1 CH (Compound # 1) E F G H Chita rice 5 5 5 5 0 5 5 5 5 0 5 5 5 5 0 and 5 5 5 5 0 5 5 5 5 0 5 5 5 5 0 and 5 5 5 5 0 5 5 5 5 0 5 5 3 5 4 13.9 g of 2-amino-4-methoxy-6-methylpyrimidine are dissolved in 150 ml of dry dichloromethane and a solution of 28.5 g of 2-biphenylylsulfonyl isocyanate in 40 ml of toluene is added dropwise over 1 hour. The reaction mixture is maintained at room temperature during the addition. After the addition was complete, the mixture was stirred at room temperature for 10 hours to complete the reaction, then the reaction mixture was concentrated to about half volume by evaporating the dichloromethane under reduced pressure, the resulting colorless crystals were filtered off, washed with a small amount of ether and dried. 34.6 g of the desired N-2-hiphenylylsulfonyl-N- (4-methoxy-6-methylpyrimidin-2-yl) urea, m.p. 199 DEG-202 DEG C., are obtained. Example 2 (Compound No. 2) 14.0 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are suspended in 100 ml of dry acetonitrile and 0.1 g of 1,4-diazabicyclo [2.2.2] is added to the suspension. octane. A solution of 28.5 g of 2-biphenylylsulfanylisocyanate in 30 ml of xylene is added dropwise over 1 hour. During the addition, the reaction is accompanied by a slight heat generation and cooling is therefore required. After the addition was complete, the reaction was allowed to proceed for 5 hours at room temperature and for an additional 5 hours at 40 ^° C, the reaction flask was allowed to cool to room temperature, the precipitated crystals were filtered, washed with ether and dried. 33.9 g of the desired N-2-biphenylylsulfonyl-N &apos;-( 4-methoxy-6-methyltriazin-2-yl) urea, m.p. 190-193 [deg.] C., are obtained. Other compounds of the invention which were prepared in an analogous manner to that described above are listed in Table 2 below. TABLE 2 о - N сн ₅ осн ₅ OCHj ОСН. 178—180 196—200 185—190 175—180 160—165 subject 2. A process for the preparation of substituted phenylsulfonylureas of the formula I according to claim 1, characterized in that the compound of the formula II X (ii) wherein X is as defined above, reacted with a compound of formula III NH2 — R (ΙΠ) in which R is as defined above, optionally in the presence of a diluent. Severograíia, n. P., Plant 7, Most Price 2,40 Kčs