BG97400A - New herbicides - Google Patents

Abstract

Herbicides are used in agriculture to combat unwanted vegetation. They represent derivatives of 4-benzoylisoxazole of general formula (c) which represents an alkyl or an optionally substituted cycloalkyl group; d2 is a halogen atom or a group selected from the group consisting of R5, -OR5, -SO2, -O (CH2) q -OR5, -SO2S a nitro group; is a halogen atom or a group selected from the group consisting of R5, -OR5, -OCH3 and -O (CH2) q -O-; r4 is a hydrogen or halogen atom or a group selected from the group consisting of R5, -OR5, -S (O) mR5, -O (CH2) a nitro group and a nitro group, with the proviso that at least one of the groups r2, r3 and r4 represents - o / cn2 / m-o5; R5 is a straight or branched chain alkyl group containing from 1 up to 4 carbon atoms, optionally substituted with one or more halogen atoms, m is 0, 1 or 2, and q is an integer from one to three.

Description

The invention relates to novel 4, benzoylisoxazole derivatives, compositions containing them and their use as herbicides. (b) The present invention provides 4-pentenyl-isoxazole derivatives of general formula (I):

(I), wherein R4 represents a straight- or branched-chain alkyl group containing from one to four carbon atoms or a 2- or 4-membered cycloalkyl group which is optionally substituted by an aldehyde group with a normal or branched chain containing up to four carbon atoms; means a halogen atom or a group selected from R5, -OR5, -S (O) mR5, -O (CH2) c-R5 and R6 represents a halogen atom or a group selected from R1, -ORg, and -CO (CH2) (R5R5 ') 4 represents a hydrogen or halogen atom or a group selected from: -OR5, -5 (O) R7, and HITP2 group, provided that at least one of the groups R3 is -O- (CH2) n- or --C (O) OR5; R5 is an alkyl group having a normal or branched chain containing from one to four carbon atoms unsubstituted by one or more halogen atoms; m denotes a pipe or cjz means an integer from one to three. The compounds according to the invention are represented by the present invention, as well as the aziocidal herbicidal activity in association with known compounds against important plant species, including Xanthium strumarium. The preferred group of compounds of general formula (I) for the preparation of the compounds of general formula (I) in which R is a halogen atom or a group selected from : R1, -OR5, 5 (O) mR5, "CO2E5 and nitro; R 4 is -O (CH 2) -DR 2; R 3 represents a hydrogen or halogen atom or a group selected from: R 1, -OR 5, -S (O) m R 5 and nitro; ie, eze or three. Thus, a preferred group of compounds of general formula (I) for their herbicidal properties are those having one or more of the following features: methyl, ethyl, 1-methyl ethyl, cyclopropyl or 1-methylcyclopropyl; R 2 represents a chlorine, bromine or fluorine atom or a group selected from: R w, -S (O) R c; R 1 represents a chlorine, bromine or fluorine atom or a group selected from: R 1 represents a straight- or branched-chain alkyl group containing from one to four carbon atoms optionally substituted with one or more halogen atoms. Another preferred group of compounds of general formula (I) having their herbicidal properties are those having one or more. the following features: R 1 is 1-methyl ethyl, 1-methylcyclopropyl or cyclopropyl; J & means a methyl, ethyl or trifluoromethyl group; at least one of the groups B2 and R4 is -5 / O / CH3, provided that they do not simultaneously mean the group: -SO-CH-; and means two. A particularly preferred group of compounds of general formula (I) for their herbicidal properties are those in which: R @ 3 represents a cyclopropyl group; means a chlorine, bromine or fluorine atom; or a group selected from: methyl, trifluoromethyl, -5 (O) MCH3; R 3 represents a chlorine, bromine or fluorine atom or a group selected from: methyl, trifluoromethyl and the group - (C 1 -C 6) -alkyl, at least one of the groups -acc -5 / 0 / ,. provided that they do not simultaneously mean the group -SO2CH2; and he got two. Also particularly preferred compounds because of their herbicidal activity are: 1. 4- [2,4-dibromo-3- (2-methoxyethoxy) benzoyl] -5-cyclopropylisoxazole; 2-, 4- [1-bromo-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5-cyclopropyl isoxazole; 3- [2-Bromo-3- (2-methoxyethoxy) -4-methylsulfonyl-5-enoyl] -5- (1-methylcyclopropyl) isoxazole; 4. 4- [2-Bromo-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5-methylisoxazole;

7 S 5. 4- [2-chloro-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5-cyclopropyl isoxazole; b) 4- [2-chloro-3- (2-methoxyethoxy) -4-methylsulphinylbenzoyl] -5-isopropylpropyl isoxazole; 7. 4- [2-Chloro-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5-methyl isoxazole; s- 4- [2-bromo-3- (2-methoxyethoxy) -4-methylsulphenylbenzoyl] -5-cyclopropyl isoxazole; 9. 4- [2-Bromo-3- (2-methoxyethoxy) -4-methylthionylbenzoyl] -5-cyclopropyl isoxazole;

10. 4- (4-bromo-2- (2-methoxyethoxy) -2-methylsulfonylbenzoyl) -5-cyclopropyl isoxazole; 11. 5-propyl-4- (2-methylsulphenyl) -3- (2-methoxyethoxy) benzoyl] isoxazole; 1.2. 5-cyclopropyl-4- (2-methylthionyl-3- (2-methoxyethoxy) -benzoyl) isoxazole; and 13. 5-cyclopropyl-4- (2-methylsulfonyl-3- (2-methoxyethoxy) benzoyl) isoxazole. The above-mentioned compounds with nomenclatures 1 to 13 are more readily utilized in the preferred embodiments. The compounds of general formula (I) are prepared by the application or adaptation of known methods (i.e. methods used so far or described in the literature (e.g., those described below). In the description hereinafter, where the indications in the formulas are not specifically indicated, it is to be understood that they have the meanings indicated above in accordance with the first assigned definition of the respective designation in the specification. The preparation methods described below can be carried out in various ways and the appropriate protecting groups can be selected depending on the desired compounds to be obtained. The compounds of the general formula (I) according to the present invention can be prepared by reacting compounds of the general formula (II)

Wherein R 1, R 2 and R 1 are as defined above and a movable group with a hydroxide amine salt. More preferred is hydroxylamine hydrochloride. Typically, L represents an alkoxy radical, for example ethoxy, or a dialkylamine such as dimethylamine. The reaction is usually carried out in a solvent medium such as ethanol or acetonitrile, optionally in the presence of an acid acceptor such as triethylamine or sodium acetate . According to the present invention, the compounds of general formula (I) are prepared by reacting compounds of general formula (III);

in kgrto OR is as defined above, with compounds of formula (iv):.

(IV) wherein R 1, R 2, R 3 and R 4 are as defined above. Typically, the reaction is carried out in the presence of a Lewis acid catalyser, for example aluminum chloride, at a temperature of from room temperature to 100 ° C. According to the present invention the compounds of general formula (I) may be prepared by reacting compounds of formula (V): M

N / V /, - X, wherein R is as defined above, and R is a carbon atom.

group or a reactive derivative thereof (such as a carboxylic acid chloride or a carboxylic acid ester or a cyano group) with a suitable organometallic reagent such as a Grignard reagent or an organolithium reagent. The usual reaction is carried out in an inert solvent such as an ether or tetrahydrofuran at a temperature ranging from 0 ° C to the reflux temperature of the mixture. The intermediates required to prepare the compounds of the general formula (I) are prepared by employing known methods. The compounds of general formula (II) are prepared by reacting compounds of the general formula (VI):

a trialkyl orthoformate such as triethyl orthoformate or dimethylformamide dialkylacetal such as dimethylformamide dimethyl acetal. Typically, the reaction with triethyl orthoformate is carried out in the presence of acetic anhydride at the boiling temperature under cooling, and the reaction with dimethylformamide dialkylacetal is optionally carried out in the presence of an inert diluent at a temperature ranging from room temperature to reflux. we are at a reflux. Typically, the reaction is carried out in the presence of an organometallic base such as triethylamine in an inert solvent such as toluene or dichloromethane at a temperature in the range of -20 ° C to room temperature. The compounds of the general formula (VI) are prepared as follows: The action of an acid chloride of the general formula (VII) or a salt

(VII) wherein R 2, R 3 and R 4 are as defined above with a salt of a compound of the general formula (VII 1)

chaia compounds of general formula (IX): (VIII),

(IX), wherein R @ 6 and R @ 4 have the meanings defined above, which are then decarboxylated to give compounds of general formula (VI). Typically, the reaction for preparing the compounds of general formula (I) is carried out in a solvent such as lower alkyl, preferably methanol, in the presence of a metal, preferably magnesium. The decarboxylation is carried out by boiling the compounds of general formula (IX) under the refluxing conditions in the presence of a catalyst such as, for example, para-toluenesulfonic acid and in an inert solvent, for example, in toluene. The intermediates of general formulas (III), (IV), (VII), (VII) and (VIII) are known or can be prepared using or adapted by known methods. Another feature of the present invention is that the bone of the compounds of general formula (I) may be capable of being formulated. . , .......... • · ···· .. .. . . .... By the cross-coupling of other compounds of general formula (I). Examples of such reciprocal conversions are described below. According to another feature of the present invention, compounds that m are one or two may be prepared by oxidation of the sulfur atom of compounds wherein m is zero. Typical oxidation of the sulfur atom is carried out using, for example, trichloroperoxybenzoic acid in an inert solvent such as dichloromethane at a temperature in the range from -40 ° C to a sufficient temperature. The following examples 1 to 2 illustrate the preparation of the compounds of general formula (i) and examples 3 to 1 illustrate the preparation of the intermediates according to the invention. 5 description the name b. means boiling point; top top. means a melting point. The JAR designation represents the characteristic of the proton nuclear magnetic resonance spectrum. PERFORMANCE IMPLEMENTATION. To a mixture of 3-cyclopropyl-2-ethoxymethylene-1- (2-trifluoromethyl) -3- (2-methoxyethoxy) -4- methylsulfonylphenyl] propan- 1,3-dione (3.5 g) and hydroxylamine hydrochloride (1.77 g) in ethanol was added with stirring with sodium acetate (1.65 g). The mixture was stirred at room temperature overnight and then evaporated to dryness. The residue was dissolved in ethyl acetate and washed with water, dried (anhydrous magnesium sulfate) and filtered. the filtrate was evaporated to dryness. The residue was chromatographed on silica, eluting with a mixture of ethyl acetate and cyclohexane (1: 5) to give 4- (2-bromo-3-

4-methylsulfonylbenzoyl) -5-cyclopropylisoxazole (compound 2) as a yellow colored oil (3.3 g), NMR (CDCl3) 1.3 (2H, m), 2.6 (1H, m), 3.3 (3H, s), 3.5 (3H, s), 3.9 , 3 (1H, d), 8.1 (1H, d), 8.15 (1H, s).

The following compounds of general formula (I) are also prepared.

k-- Compound No. *, B2 B2 * 4 t. 1 H NMR (CDCl 3):? 1 (cyclopropylpropyl) 2 (CH 2) 20Me B t * 1.15 (2H, m) 1.3 (2H, m) , 75 / 2H, f / 4.1 / 2H, 1 / 6.8 / 1H, d / 7.5 / 1H, d / 8.1 / (3H, s), 3.2 (3H, s), 3.9 (3H, s) , 8 (2H, s), 4.4 (2H, d), 7.2 (1H, d), 8.0 (1H, s) 2.6 / 3H, S / 3.3 / 3H, 3 / 3.45 / 3H, S / 3.8 / 2H, 4.4 / 2H, t / (1H, d) 8.1 (1H, s), 5-cyclopropyl C10 (CH2) 20 Me is SO4, 81.4-82.6 DEG C is isopropyl C10 (CH2) 84.2-86.2 ° C 7 MeCo / CH 2 / 20Me ... SO 4 -cyclohexane 107.2-107, S ° C 8 cyclopropyl in C 2 O / CH 2/2 OMe SMe 94.4-94.8a C 10 cyclo - Propylene SO2 O / CH2 / 20 Me is Bp 104, 2-105.2 ° C 11 'CYCLO-' propyl SMeO / CH 2/20 Me H 59-62 ° C NOTE: Me = methyl group 10

EXAMPLE 3 3-Chloroperoxybenzoic acid (50-60%) (1.3 g) was added to a solution of 5-cyclopropyl-4- [2- bromo- 3- (1.9 g) in dichloromethane) while maintaining the temperature at about -15 DEG C. The mixture was stirred at -15 DEG C. for 1 hour at room temperature

W for 1 hour. The solution was diluted with brine and then washed with a solution of sodium bisulfite (2P), then washed with water. The organic layer was dried (anhydrous magnesium sulfate) and filtered. The filtrate was evaporated to dryness. The residue was purified by dry column flash chromatography, eluting with a mixture of ethyl acetate and cyclohexane (1: 5) to give 5-cyclopropyl-4- [2-bromo-3- (2-methoxyethoxy) -4-methylthionylbenzoyl] isoxazole (compound 9), (1.52 g) as a white solid with m.p. 36.2-37.0 ° C. In a similar manner, the following compounds were prepared: 5-cyclopropyl-4- (2-methylthionyl) -3- (2-methoxyethoxy) benzoylisoxazole (Compound 12) 82 to 84 ° C; 5-Cyclopropyl-4- (2-methylsulfonyl) -3- (2-methoxyethoxy) -benzoyl-isoxazole (compound 13) 111-1.14 ° C. . EXAMPLE PERFORMANCE. 3. A mixture of 3-cyclopropyl-1- (2-bromo-3- (2-methoxyethoxy) -4- methylsulfonylphenyl) propane- 1,3-dione (7.5 g) and triethylorthoformate (10.3 g) in acetic anhydride was stirred and heated under reflux for 3 hours. The mixture was evaporated to dryness and the residue was treated with xylene and evaporated again to give crude 3-methylpropyl-1- 2- (5-bromo-3- (2-methoxyethoxy) -4-methylsulfonylphenyl) -2-ethoxymethylenepropane-1,3-dione (3.5 g) as an off-white brown oil. Similarly, from appropriately substituted excipients · · · · · · - · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · The following compounds are obtained (without purification).

Or R 2 is a cyclopropyl group or a cyclopropyl group or a cycloalkenyl group, / CH 2/20 Pa 50 / is selected from OP CI 0 / CH 2 / 20Ha S0 71 is. cyclohexyl Cyclopentyl Cyclopentyl chloride Cycloheptyl Acetyl Cyclopropyl Oxalyl Cyclopropyl Oxalyl Cyclohexyl Cycloheptyl Hydroxypropyl Cyclopropyl Cycloheptyl Cyclopentyl Cycloheptyl Oxalyl Cyclopropyl Oxalyl Cycloheptyl Ester Cycloheptyl Acetyl Ester Ester -4-methylsulphonylbenzoyl] -3-cyclopropanecarboxylic acid (10.2 g) and 4-toluenesulfonic acidotoluol are stirred and heated under reflux for 2 hours. The cooled mixture is 2- [2- 2- (2-propyl-3-oxo-butyric acid (2 g) is dry, washed with water, dried (Na2 SO4) • * «· · · ········ · · · · · · · · · · · · · Незиев. The filtrate was evaporated to dryness to give 3-cyclopropyl-1- (2-bromo-3- (2-methoxyethoxy) -4-t-butylsulfonylphenyl) propane-1,3- dione , 5 g) as a dark brown oil, NMR (CDCl3) 0.9 (4H, m), 1.5 (1H, m), 3.1 (3H, s) 3.6 (2H, t), 4.2 (2H, t), 5.7 (1H, s), 7.15 (1H, d), 7.8 (1H, d). From appropriately substituted starting materials, the following compounds are similarly prepared.

· · · · · · · · · · · · ························································ 2 3 > C NMR (m.p. cyclo-propyl C10 / CH2 / 20Me. (1H, m), 3.9 (3H, s), 4.2 (2H, t), 4.6 (2H, 4 / 1H, d / 7,9 / 1K, d / 1-Methoxypropyl V 0 / CH 2 / 20Me 50 1 is 1,2 / 2H, m / 1,5 / 2H, m / / 3H, s / 3.6 / 3H, s / 3.8 / 3H, s / 4.15 / 2H1 / 4.7 / 2H, 8.3 / 1 H, d / Me O / CH 2/2 / MeSO 4 2.4 / 3K, S / 3.5 / 3H, S / 3.7 / (1H, d / 8, 15 (1H), d) cyclopropyl C10 (CH2) 2 O, MeSO2 N1, 1 (4H, m), 1.7 (1H, m), 3.5 (3H, s), 3.5 (3H, s), 3.8 (2H, s / 7.3 / 1K, d / 7.7 / 1K, d / iso-propyl C10 / CH2 / 20Me SO3Me 1,1 / 6H, d / 3K, s), 3.6 (2H, t), 4.3 (2H, s), 7.7 (1H, s) 1H, d) (MeOH / CH 2), 20Me SO 4 = 2.4 / 3H, S / 3.5 / 3K, s / 3.7 / 3H, / 2H, t / 6.0 / 1K, s / 7.4 / 1H, d / 8.0 / 1H, d / cyphopropyl / , 8 / 1H, M / 2.5 / 3K, S / 3.5 / 3H, s / 3.8 / 2H, t / 4.2 / 2H, / 2K, m / cyclopropyl propyl SO2 O / CH2 / 20Me Br 1.0 / 4H, m / 2.0 / 1H, m / 3.3 / 3H, , 9 (2H, t), 4.4 (2H, t), 5.75 (1H, s), 7.3 (1H, d) o- propyl-L 5Me 0 / CH 2 / 20Me H - NOTE: Me = methyl

· · · · · I - 14 - · · · · · * ·

To a mixture of 3-cyclopropyl-3-oxopropanoic acid tertiary butyl ester (4, 5 g) and magnesium (0.63 g) in methanol is added with stirring carbon tetrachloride (1 ml) as the reaction mixture is stirred for 0.25 hours and evaporated to dryness.The residue is dissolved in acetonitrile and solution of 2-bromo-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl chloride in acetonitrile (50 ml) was added and the resulting mixture was stirred at room temperature for 2 hours. The resulting solution was dried (anhydrous magnesium sulfate) and filtered The filtrate was concentrated in vacuo and the residue was suspended in toluene.The slurry was washed with 2N HCl and then with water.The resultant organic solution was dried (anhydrous magnesium sulfate) and filtered.The filtrate dried to dryness to give 2- [2-bromo-3- (2-methoxyethoxy) -4-methylsulfanyl-benzoyl] -3-cyclopropyl-3-oxopropanoic acid tert.-butyl ester (10.27 g) / in brine, brown color, bulk substance. In the same way, the following compounds were prepared:

15 ·································································································

The reaction mixture was cooled to room temperature and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was stirred at room temperature for 2 hours. 20 mg of SO2 -toluene cyclopropyl C10 / CH2 / 20m2 SO2He. CH3 -CH2 -CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 SO 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 2 CH O / CH 3 OH O-CH 3 CH 3 OH Benzoylchlopids are prepared by heating the corresponding substituted benzoic acids at reflux with thiolsulfide for 3 hours. EXAMPLE 6 2-Bromo-3- (2-methoxyethoxy) -4-methylsulfenylbenzoic acid ethyl ester (24.3 g) was added to a solution of potassium hydride (9.1 g) and industrial methylated spirit (300 ml). The resulting mixture was heated at reflux for 4 h after allowing to cool to room temperature overnight. The mixture was evaporated and the residue was dissolved and washed with ether. The aqueous layer was acidified to pH 1 with 2N HCl and extracted with ethyl acetate. The mixture was poured into ethyl acetate with water (anhydrous sodium sulfate) and filtrate. The filtrate was dried to dryness to give 2-bromo-3- (2-naphthoxy) -4-methylsulphinylbenzoic acid (19.4 g) as a white solid (1.6 g). · · · · · · ································································································ (3H, s), 3.26 (2H, t), 3.8 (2H, t), 7.0 (3H, 2H, m) Similarly, 4-bromo-3- (2-methoxymethoxy) -2-methylsulphonylbenzoic acid was obtained as a white solid, mp 156-157.8 ° C, starting compound ethyl 4-bromo-3- (2-phenoxyethoxy) -2-pentylsulponyl-enzoenoic acid. YES 7. Ethyl 4-formyl-3- (2-methoxyethoxy) -2-methylsulfenyl benzoic acid (5.0 g) was stirred in acetic acid (3.0 ml) and acetic anhydride The mixture was stirred at 0 ° C for 1 hour and then overnight at room temperature. The mixture was then heated for 1 hour at 85 ° C. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water, then pellet with ferrous sulfate, and finally with water. The organic extract is dried (anhydrous magnesium sulfate) and filtered. The filtrate was evaporated to dryness to give 4-bromo-3- (2-methoxyethoxy) -2-methylsulphonylbenzoic acid ethyl ester (4.7 g), IAP (CDCl3) 1.8 ), 3.4 (3H, s), 3.8 (3H, s), 4.15 (2H, t), 4.3 (2H, q) (H, d), 7.85 (1 H, d). EXAMPLE 8 2,4-Dibromo-3- (2-methoxyethoxy) benzoic acid ethyl ester (w) was stirred in dimethylformamide (30 ml) with potassium carbonate (36 g). To the resulting suspension was added a solution of thionyl chloride (1.3 ml) in dimethylformamide (20 ml). The resulting mixture is obtained

Stir overnight at room temperature. It is then treated with ether and the mixture is washed with water, dried (anhydrous magnesium sulfate) and filtered. the filtration was evaporated to dryness. The residue was purified by column chromatography over silica, eluting with ethyl acetate and cyclohexane (1: 20), to give ethyl 1,7-benzisoxazole. 4-Bromo- 3- (2-methoxyethoxy) -2-methylsulfanylbenzenesulfonate. (3.5 g) of an oil which was not further characterized. PRINCIPLE 9. 2- [3- (2-Methoxyethoxy) -2-methylsulfanylphenyl] -4,4-dimethyl-2-oxazoline (48.7 g) solution of hydrochloric acid (700 ml) at 90 ° C. The mixture was stirred at 90 ° C for 3 hours, cooled to room temperature and extracted with ethyl acetate. The organic extract is washed with water, dried (anhydrous magnesium sulfate) and filtered. The filtrate was evaporated to dryness to give 3- (2-methoxyethoxy) -2-methylsulphenyl-benzoic acid as a golden oil (40.9 g), Yield (CDCl3) 2.5 (3H, s) (2H, t), 7.1 (1H, m), 7.4 (1H, m), 7.6 (1H, m) ). EXAMPLE 8 A solution of 2- [3- (2-methoxyethoxy) phenyl] -4,4-dimethyl-2-oxazoline (63.4 g) in tetrahydrofuran was cooled to -40 ° C under an inert atmosphere. To the solution was added n-butyl lithium (122 mL of 2.5 m). The resulting mixture was stirred at -15 ° C over Tcc, then re-cooled to -40 ° C. Addition. dimethyl disulfide (52.7 g), then the reaction mixture was allowed to warm to room temperature and stirred for 1 hour. Add saturated ammonium chloride solution and extract with ether. The organic extract was washed with water, dried (anhydrous magnesium sulfate) and filtered. The filtrate was evaporated to dryness and the residue was triturated with hexane to give 2- [3- (2-methoxyethoxy) -2-methylsulphenyl phenyl] -4,4-dimethyl-2- (56.5 g) as a powdered substance, m.p. 44.4 DEG -46 DEG-4 DEG C., was obtained. PRINCIPAL IMPLEMENTATION 1T>. N - [2 - [(1,1-dimethylethyl) -3- (2-methoxyphenyl) amino] · · ···································································································· Was stirred at 0 ° C for th hour. Thionyl chloride (90 mL) was added over 1 hour. The resulting solution was stirred at 15 ° C for a further 1.5 hours and dry diethyl ether was added. The excess solvent was removed in vacuo and the residue was triturated with diethyl ether, washed with 2N sodium hydroxide solution and the organic phase was separated. The organic extract is washed with zinc sulfate (anhydrous magnesium sulfate) and filtered. the filtrate was evaporated to dryness and the residue was distilled under reduced pressure. There was obtained 2- [3- (dimethoxyethoxy) phenyl] -4,4-dimethyl-2-oxazolidine (66 g). 164-178 ° C at a pressure of 1.5 mm Hg. EXAMPLE 12 12. 2-Amino-2-methylpropan-1-ol (57.6 g) was dissolved in dichloro-

The mixture was cooled to 0 ° C. A solution of 3- (2-methoxyethoxy) benzoyl chloride (67.8 g) in dichloromethane was added and the solution was stirred overnight at room temperature during which time a precipitate . The mixture was filtered and the filtrate was evaporated to dryness to give N- (2-hydroxy-1,1-dimethylethyl) -3- (2-methoxyethoxy) benzamide (95.9 g) NMR (CDCl3) 1.4 (6H, s), 3.5 (3H, s), 3.65 (2H, s), 3.7 (2H, t) 5.4 (1H, s), 6.3 (1H, s), 7.0 (1H, m), 7.3 (2H, m). Exemplary Performance. Of 3- (2-methoxyethoxy) benzoic acid (72.9 g) and thionyl chloride (19 g) were refluxed together for 1.5 hours and then allowed to cool overnight. the mixture was evaporated under reduced pressure. The residue was deprotected under reduced pressure. There was obtained 3- (2-methoxyethoxy) benzoyl chloride (67.7 g), m.p. 130 ° C at a pressure of 0.4 mm But. EXAMPLES 14. 2-Methoxyethyl 3- (2-methoxyethoxy) benzoic acid (3 g) was dissolved in industrial methylated tannate and added · · · · ································································································· 2 1 * 1 sodium hydroxide solution and heated to reflux for 1.5 hours. The mixture was allowed to cool to ice and ice was added. The resulting mixture was washed with ether, the aqueous layer was acidified to pH 1 with hydrochloric acid and the resulting mixture was filtered. The residue is washed with water and dried in the air. The residue is recrystallized from ethanol. ether and petroleum ether (m.p. keel. 40-B5 to give 3- (2-methoxyethoxy) benzoic acid (36 g) as a white solid, m.p. 79.6-81 ° C. -fefe. EXAMPLE 15 3. 3-Hydroxybenzoic acid (73 g) was dissolved in dimethyl formamide, followed by potassium carbonate (TbO), 2-chloroethyl methyl ether (200 g) and potassium iodide (3.8 g). The mixture was heated to 42 hours at 72 ° C. After cooling, the mixture was poured onto ice and extracted with ether. The organic extract was washed with 2N sodium hydroxide solution, water, brine, dried (anhydrous magnesium sulfate) and filtered. The filtrate was evaporated to dryness to give 3- (2-methoxyethoxy) benzoic acid 2-methoxyethyl ester (1.35 g) which was further purified. The invention also provides a method of controlling weeds (i.e., undesirable vegetation) at a site whereby a herbicidal effect of at least one isoxazole derivative of general formula (i) is applied to the place where the weeds are inhabited. For this purpose, isoxazole derivatives are usually used in the form of herbicidal compositions (i.e. together with suitable diluents or carriers and / or surfactants suitable for use in herbicidal compositions (e.g., those described below). The compounds of general formula (I) exhibit herbicidal activity against dicotyledonous (i.e. deciduous / one-sided / s / • · • · · · · · · · W · · ······· · · · · · · · ···· 20 · · · · · · · · · · · ································································································································································································································· . By the term " pre-emergence application " is meant the application of the seed to which the weed or germination seeds are present prior to the emergence of the entanglements above the soil surface By the term "post-emergence application" is meant application to the area or exposed parts of the weeds which are For example, the compounds of the general formula (I) may be used to combat the following tazular zidases: broadleaf slaughters, for example:

AbutiTon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Galium apar'ine, Ipomoea spp., E.g., Ipomoea purpurea, Sesbania exaltata,

Sinapis arvensis, Solanum nigrum and Xanthium strumarium

grass clusters, for example:

Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloacrus-galli, Sorghum bicolor, Eleusine indica and Setaria spp.

Setaria faberii or Setaria viridis and spice, e.g. Cyperus esculentus. The rate of application of the compounds of the general formula (I) varies depending on the composition of the plexiglas, the compositions used, the time of application, the climatic and soil conditions and the growth rate of the application the area of cultivated plants / the nature of the cultural heritage of which the breed grows, the rate of application must be sufficient to control the pests without causing significant and permanent damage to the crop plants. As we have seen before, the sectors listed above are 0, 01 kg and 4 kg of the 1 ha ha, giving good results. It goes without saying that higher and lower application rates are used depending on the problem. · · · · · · - · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · The compounds of the general formula (1) can be used to effectively control the growth of weeds, for example, for controlling the growth of these species mentioned above before or after emergence in a direct or indirect manner, for example by direct or indirect spraying on the weeds of the weed, which is an area that is used or will be used for crop growing such as wheat, barley, oats, corn and rice, soybeans and low-fat beans, peas, ice cream, cotton, peanuts, linseed, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet and permanent or sown lawns before or after sowing the crops or before or after emergence of the crops. For selective control of weeds at the site of attack by slaughters, Koefo represents the utilized area or area to be used for growing crops, for example the crops mentioned above, suitable rates of application between C, G1 kg and 4.0 kg, and preferably between 0.01 kg and 2.0 kg of the active ingredient per 1 ha. The compounds of general formula (I) may also be used to control weeds and especially those weed. more pre-or post-emergence application to orchards and other areas, such as wooded forests, forests and parks and plantations, for example, sugar plantations, oil palm and rubber. For this purpose, they may be applied either directly or indirectly (for example, by direct or indirect dispersion) on the seeds or on the soil but which are expected to occur before or after planting the trees or plots at the rate of application and the range of from 0.25 kg to 5.0 kg and preferably between 0.5 kg and 4.0 kg of the active compounds of the general formula (I) may also be used to control weeds, and in particular, We have 1> 22 • · • · · · · ·

In the places where there is plenty to cultivate cultural herds, but which is desirable to combat weeds . Examples of such non-crop areas are airports, industrial beaches, railways, roadside strips, riparian coastlines, other waterways, scrub and fallow land or uncultivated land, and in part- where it is desirable to kill weeds in order to reduce the risk of fires when used for a purpose requiring a multiple complete herbicidal effect, active compounds are normally used at doses higher than those used for treatment of areas, in which they cultivate crop plants, as described above. The liquid dose depends on the vegetation and the desired effect. Typically suitable for this purpose is pre-emergence or pre-emergence application and preferably administration by emergence by direct or indirect means (e.g., by direct or indirect dispersion) at application rates in the range of 1.0 kg to 20.0 kg and for preferably from 5.0 kg to 10.0 kg of actives per 1 ha. When used for weed rods by pre-emergence application, the compounds of general formula (i) can be sown in the soil in which the weeds are expected to germinate. One useful feature of the compounds of the general formula (I) is that when they are used to combat sneezing by post-nasal administration, ;;; With the weeds, the compounds of the general formula (i) will normally come into contact with the soil and may also exercise control prior to postponing the later emerging weeds to the soil. When a particularly long-lasting, needle-bearing weed is needed, then the application of the compounds with the sap. / can be repeated. The present invention also provides compositions suitable for use in the manufacture of a medicament for the manufacture of a compound of the formula (I) in the form of a compound of the formula (I), and preferably, but dispersed in, or for the preparation of compatible and acceptable diluents for carriers or carriers and / or active substances (i.e. diluents or carriers and / or surface-active agents of the masonry normally used in the art and suitable for use are herbicidal compositions and which are compatible with the compounds of the general formula (II). The term "chemical-dispersion" means those compositions in which the compounds of formula (I) are dissolved in the other components. The term "herbicidal compositions" is used in a broad sense and excludes only the compositions which are The compositions preferably contain from 0.05 to 90 parts by weight of one or more of the compounds of the general formula (I) The herbicidal compositions may contain a carrier or carrier, and The surfactants, which may be components of the herbicidal compositions according to the present invention, may be of the ionic or nonionic type, as well as of the nonionic surfactants, for example sulphoricinates, quaternary ammonium derivatives, products based on ethylene oxide condensates with alkyl and polyarylphenols, for example nonyl or octyl phenols or esters of anhydrous sorbitol and carboxylic acids which are obtained. in soluble form by esterification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulfuric acid and sulfuric acid esters, such as, for example, diazonyl dioctyl sodium sulphonosuccinates and alkaline earth metal salts, The present invention relates to the production of high molecular sulfonic acid derivatives such as N < RTI ID = 0.0 > propranatrium and calcium lignosulfonates < / RTI > and sodium and calcium alkyl -benzenesulfonates. The herbicidal compositions according to the present invention comprise up to 10 wt%, for example from 0.05 to 10 wt% surfactant, but if desired the herbicidal compositions according to the present invention may also contain higher concentrations of the surfactant, for example up to 15% by weight of liquid-soluble suspension concentrates and up to 25% by weight in liquid, water-soluble concentrates. Suitable solid diluents or carriers may be aluminum silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorbent soot and clay such as kaolin and bentonite. Preferably, the solid compositions / which may be in the form of? powders, granules or wettable powders) are prepared by grinding the compounds of general formula (I) with solid diluents or by saturation of the solid diluents or carriers with solutions of the compounds of the general formula (I), volatile solvents, evaporation of the solvents and, if necessary, -packing the products so that they get powders. The granular compositions are prepared by adsorbing the compounds of general formula (I) dissolved in suitable solvents which may be volatile on solid diluents or carriers in granular form and, if desired, evaporation of the solvents or by granulation of the compositions in the form of a powder obtained as described above. The solid pesticidal compositions of the present invention may contain humectants or dispersants (for example, those from the above described solids) which can also serve as diluents or carriers. The liquid compositions are in accord with the invention of the flora The aqueous solutions of aqueous, organic or aqueous-organic solutions, suspensions, emulsions, which exclude surfactant, suitable liquid diluents for incorporation of the composition of the liquid compositions water, clioles, tetrahy rofurfurilsv alcohol, acetophenone, cyclic-lsheksanon, isophorone, toluene, ksmlol, mineral, animal, and pac-titelni oils and light aromatic and naftensvi fractions of oil / Toi how mixtures of these diluents /. Surfactants are substances which can be incorporated into the liquid compositions, they may be ionic or nonionic (for example of the types described above) when they are liquid to replace the diluents or carriers. ) The powders, dispersible granules and the liquid formulations of the concentrate may be diluted with water or other suitable diluents, for example mineral or vegetable lubricants, optionally in the form of liquid concentrates in which the diluent or carrier is an oil, compositions ready for administration are obtained. If desired, the liquid formulations of the compounds of general formula (I) may be administered in the form of semi-emulsifiable concentrates containing the active substances dissolved in the emulsifiable substances or in solvents containing emulsifiable substances which are compatible with the active substances, the simple addition of water to these concentrated concentrates. until the composition of the compositions to be used. Liquid concentrates in which the diluent or carrier is an oil may be administered without further dilution, using electrostatic spraying techniques. The herbicidal compositions according to the present invention may also contain, if desired, conventional additives such as adhesives, colloids, thickeners, penetrants, stabilizers, pastilles, anti-caking agents, coloring agents. · · · · · · · ································································································ And corrosion inhibitors. These additives may also serve as carriers or diluents. The percentages given below, unless otherwise indicated, are by weight. Preferred herbicidal compositions according to the present invention are aqueous suspension concentrates containing 10 to 70 z'3 of one or more of the compounds of general form; - (I), from 2 to 10% of a surfactant, 0 to 0.1 to 5, of CrBCTMTBzT and from 15 to 87.9% of water; and powders containing from 10 to 90% of one or more of the compounds of general formula (I), from 2 to 10% of the surfactant and from 8 to 98% of a diluent or carrier; water-soluble or water-soluble sorbents and powders which contain 10 to 30% of one or more of the sterilizes of the general formula (x) and 2 to 40% of sodium carbonate and from 0 to 38% of a solid diluent; liquid water-soluble concentrates containing from 5 to 50%, for example from 10 to 30% by weight. or picked up by a man. (I), from 5 to 25 of a surfactant and from 25 to 90%, for example, from 45 to 85% of an immiscible solvent, for example dimethylformamide. or cm3 of water-miscible solvent and water; liquid emulsifiable suspension concentrates, the mud comprising from 10 to 70% by weight of one or more of from 5 to 15% by weight of a compound of general formula (I), from 0.1 to 5% by weight of thickener and from 10 to 84% , 9% organic solvent; ) granules containing from 1 to 90%, for example from 2 to 10%, of one or more of the compounds of general formula (I), 0.5 to 7%, for example from 0.5 to 2% of the surfactant, and from 3 to 93.5%, for example from 8% to 97.5%, a granular carrier and emulsifiable concentrates containing from 3.05 to up to%, 27 • • • • • Preferably, from 1 to 60 of one or more of the compounds of general formula (I), from 0.01 to 10%, preferably from 1 to 10% of a surfactant and from 9.99 to 99.94%, preferably of 39 to 98, 99% of an organic solvent. The herbicidal compositions of the present invention may also contain the compounds of general formula (I) in combination with, and preferably homogeneous, dispersed in one or more other pesticidally active compounds and in dividing one or more compatible pesticidally acceptable diluents or carriers, surfactants, and conventional adjuvants as described above. The herbicides for such pesticidally active compounds which can be used in the herbicidal compositions of the present invention are herbicides, for example, for enhancing the scope of the target species to be controlled, for example: alchlorochloride (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine), bromoxynil (3) , 5-dibromo-4-hydroxybenzonitrile), chlorotoluron / N '- (3-chloro-4-methylphenyl) -N, N -dimethylsilylamide, cyanazine / 2chloro-4- methyl-ethyl) amino) -6-ethyl amine-1,3,5-triazine, 2,4-D (2,4-dichlorophenoxyacetic acid), dicamba (3,6-dichloro-2-methoxybenzoic acid), difenzoquat (1,2- diethyl-3,5- diphenylpyrazole salt) N-2- (N-5-enyl-3-chloro-4-fluoroanilino) -propionic acid methyl ester, fluorometuron N, N- N, N-diisopropylethylamine / N, N-diisopropyl-N, N-dimethylcarbodiimide, insecticides , for example, synthetic pyrethroids, for example permethrin and cyperptrin, and fungicides, for example carbamates, such as N- (1-butylcarbamoyl-benzimidazol-2- / Carbamic. acid and triazolinone. 4-chloro-phenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-one. t. The pesticidally active compounds and other biologically active compounds which may be included in the present invention include the schisticidal compositions of the present invention, for example, + the strands referred to above and which are acidic may be used to treat conventional derivatives, for example, alkaline earth metal salts, amines and esters. The present invention also provides an article containing the most preferred derivative H3 (I) or a herbicidal composition as hereinbefore defined, and preferably a herbicidal concentrate which has the formula The said article contains at least one derivative of the isoxazole of the general formula (I) contained in the container or the said herbicidal composition, such as given and instructions explaining the manner in which the aforementioned derivatives of general formula (i) or herbicidal compositions, a container These containers must be used to control weeds Containers generally are of a kind commonly used for the storage of chemical products which are solid at normal ambient temperatures and for herbicidal compositions especially under the form For example, they can be metal cans and drums which can be lacquered from plastics, bottles or glass containers, and when the contents of the container are a solid, for example granules, gel-like compositions, boxes, e.g. Ribbon of cardboard, plastics and metal lobbies. The volume of the containers normally needs to have sufficient capacity to collect the quantities of the isoxysil or herbicide compositions which are sufficient to process at least a few acres of land to kill the weeds, but they do not. must exceed the size that is available: the conventional methods. Instructions must be a container: physical 3 skis 29 ··········································································································· · · ···· ···································· For example by drinking directly on top of the label or the label fixed on the container. The guide must indicate , хр. the contents of the container, after dilution, if necessary, to be used for destroyed vesicles at an application rate of between 0.01 kg and 20 kg of the occluding substance per 1 ha in the manner and for the purpose described Hereinafter the following herbicidal compositions illustrate the present invention. PRINCIPLE OF EMBODIMENT 15. A soluble concentrate is obtained as an active ingredient (compound 1). A solution of potassium hydroxide, 33% w / v Tetrahydrofuran or an alcohol (TFA) stirring the tetrahydrofurfuryl alcohol, the active ingredient (compound 1) and 50 volume percent of water, dropping the potassium hydroxide solution slowly until the pH is 7-8, then the volume is added to the soda. Likewise, soluble concentrates, kg of 20% w / v, 10% w / v, 10% w / v, are added to 1, replacing the isoxazole (compound 1) with another formulas. SUMMARY OF THE INVENTION 17. A wettable powder is prepared from: Active Ingredients (Compound 1) Sodium dodecylbenzenesulfonate Sodium lignosulphate Sodium formaldehyde adiphyl naphthalenesulfonate microfine silicon dioxide inulin with 50 weight / weight 3 weight / weight 5 weight / weight 2 weight% 3 - w / w is 37% w / w w w w w w w w w w w w w w w w w w w w w w w w

· · · · · · · V · · · · · · · ······················································································· In the same way, wettable molds may be introduced into the air jet mill in a manner similar to that described in U.S. Pat. (1) with other compounds of the general formula (I) and (I) .Preparation of the active substance (compound 1) Sodium dodecylbenzenesulfonate Lactobacillus sodium bicarbonate Sodium bicarbonate by mixing The present invention also provides a process for preparing other water-soluble powders by replacing isoxazole (compound) with other compounds of the general formula (i), in a manner similar to the general formula (i), in which the compound (s) In general, suitable compounds for the treatment of plants are dissolved in acetone, whereby dilutions are obtained with rates equivalent to application rates. to 4000 g of the test compound per 1 ha / g / ha. These solutions are sprayed with a standard laboratory herbicide, delivering the equivalent of 290 liters of spore liquid for 1 ha. b / Pre-emergence application Seeds are sown in a deep-fat, 75 mm2 deep-sealed container. and an area of 70 mm with non-tertiary seating. The quantities of Satan in each individual vessel are as follows - 31 - Weed species 1 / Broadleaf weedsAbutilon theophrastiAmaranthus retroflexusGalium aparineIpomoea purpureaSinapis arvensisXanthium strumarium 2 / Grass weedsAlopecurus myosuroidesAvena fatuaEchinochloa crus-galliSetaria viridis 3 / Ostritsa

Cyperus esculentus Crop plants 1 / Corn rootworm Cotton soybean 2 / Grass Maize I Rye Fennel Approximate 6poi seeds / vessel 20 10 10 15 2. 15 10 15 20. With the compounds according to the invention the surface of the soil is sown, (a). For each treatment, a separate vessel was determined for each culture and for each; weed control as well as for non-spray controls and controls sprayed with acetone only. After treatment, the vessels are placed on a capillary ash-greenhouse and irrigated on top of a visual evaluation of the Y2 'of K1'; • · · ······· · · · · · · · · · · · ·

The ultraviolet is carried out at 2 * - * 24; daylight saving time. The results are expressed as% of the population of the growing or, respectively, of the corresponding crop or pseudo-naive compared to the control vessels. a / application after decay

John Innes

Amaranthus U o 2 L and T 3 and X w / L 7 D DT 2 C 2 8 C 2/7 D 2 D DiChTts of a depth of 7 5 gm and an area of 7 m. .kins of the wall; , which is planted after the germination and was transferred to a saddle before a spraying. After this, the plants are grown in the greenhouse until they are ready for spraying plants intended for planting. The number of plants per each vessel is as follows: 1 / Broadleaf weeds Fractal wall of the plant Abutilon theophrasti 3. 1g2 leaves Amaranthus retroflexus 4 1-2 l and Galium aparine 3 I and c. Ipomoea purpurea 3 1-2 liters Sinapis arvensis 4 2 leaves. Xanthium strumarium 1 2-3 leaves Grass weeds Rabbit species Number of strains 3 1 1 -. H 2 P orts / vessel Alopecurus myosuroides 8-12 1-2 l Avena fatua 12-18 1-2 leaves Echinochloa crus-galli 4 2-3 leaves Setaria viridis 1.5-25 1-2 leaves Dctp% Fowl the number of CWDs ". N 2 Stage of growing up; of isolation;

Cyperus esculentus leaves - 33 - 1 / Wild chocolate - Crop plants Soya 2 / Grass • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • Cultural Growth Maize Orchard Flower Growths / Bowl 2 4 Phase of Stage 2 to 2-3 Leaves 2-3 Sheets The compounds intended for plant treatment are applied as described in (a) . For each treatment, a separate vessel is determined for each crop and weed species, as well as for untreated controls and controls sprayed with acetic acid. After treatment, the pots were placed on green capillary pans and topped once every 24 hours, then irrigated under controlled conditions, 20-24 days after the spray, made a visual assessment of the damage to the cultures and the pits. The results are expressed as a percentage decrease in growth or injury of culture i.i. a comparison with the plants in the control vessels. The compounds according to the invention at a rate of application of 4 kg / ha or more unfortunate show excellent herbicidal activity along with the resistance of cultures to the used species of species of the experiments. When a rate of 1000 g / ha of the compounds from 1 to T3 is applied before or after emergence, at least a 90% reduction in the growth of at least one weed species is obtained.

Claims (8)

.--- ··· · · ······· * · · · · ·. · ·································. . ., .... ·····························. ·. PATENT CLAIMS 1. Derivatives of 4-benzoylisoxazole of general formula (I): / V wherein R1 is a normal or branched alkyl group containing from one to four carbon atoms or a three or four membered alkyl group which is unsubstituted or substituted by a normal or branched chain alkyl group containing 4 carbon atoms atom "means a halogen atom or a group selected from: R5, -OR5, -OR5, -OR5, -CH2C5 and -CHR5, and R5 represents a halogen atom or group selected from: R @ 4 represents a hydrogen or halogen atom or a group selected from: R @ 1, R @ 5, R @ 5, R @ 5, R @ 0 / CH 2 / OR in situ group, with the proviso that at most, R 1 is a group of R 1, R 2 and R 4 is -O (CH 2) n -OR 5; R 5 is a straight- or branched-chain alkyl group containing from one to four membered ring atoms optionally substituted by one or more halogen atoms; means zero, one or two, and means an integer from one to three. 2. Derivatives according to claim 1, wherein R1 is-Q (C1-C4) -OR9. Derivatives according to Claim T or 2, characterized in that R 1 represents a halogen atom or a group selected from: R 1 -OR 5, -S (O) m R 5, -CO 2 R 5 and nitro; R1 is a hydrogen or halogen atom or a group selected from: ROR5, -S (O) mR5 and nitro, and means two or three z is - (CH2) n - ····················································································· Derivatives according to claims 1, 2 or 3, characterized in that they possess one or more of the following features: R represents a methyl, ethyl, 1-methylethyl, cyclopentyl or 1-methylcyclopropionate. group; R < 1 > represents a hydrogen atom, a bromine atom or a fluorine atom or a group selected. of R 1 and R 5, R 5, R 5; R 1 represents a hydrogen atom, a bromine atom or a fluorine atom or a group selected from: R 1 and -S (O) R a; R 2 represents a straight-chain or branched acyclic group containing from one to four carbon atoms optionally substituted with one or more halogen atoms. Derivatives according to any one of the preceding claims, characterized in that they have one or more of the following features: R represents 1-methylethyl, 1-methylcyclopropylidicylcaptopropyl group; R1 is a methyl, ethyl or trifluoromethyl group; At least one of the groups R0 and R5 denotes -5, 0, CH3, 4, 4, with the proviso that R1 and R2 do not mean simultaneously, the group -S02CH3 'signifies two. 6. A compound according to any one of the preceding claims, wherein R1 represents a cyclopropyl group; R2 represents a hydrogen atom, a bromine atom or a fluorine atom; or a group selected from the group consisting of a chlorine, bromine or fluorine atom, or a group selected from methyl, trifluoromethyl, and the like, at least one of the groups R 1 and R 2, with the proviso that R2 and R5 do not mean simultaneously. -SO2CH3; and ψ denotes two. ° / s2 / -or5; of methyl, trifluoromethyl and -5 (O) CH3; GH HH 3 • · • · · · · · · · · · · The derivatives according to claim 1 or 2, characterized in that they are: 4- [2,4-dibromo-3- (2-methoxyethoxy) benzoyl] -5-cyclopropyl isoxazole 4- [2- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5-cyclopropylisoxazole 4- (2-bromo-3- -cyclopropyl / isoxazole; 4- [2-bromo-3- (2-methoxyethoxy) -4-methylsulphonylbenzoyl] -5-methyl-oxazole; 4- (2-Chloro-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl) -5-cyclopropyl isoxazole; 4- [2-chloro-3- (2-methoxyethoxy) -4-methylsulfonylbenzoyl] -5- (1-methyl-ethyl) isoxazole; 4- [2-chloro-3- (2-methoxyethoxy) -4-methylsulphonylbenzoyl] -5-methyl-oxazole; 4- (2-bromo-3- (2-methoxyethoxy) -4-methyl-phenyl) -benzoyl] -5-cyclo-propyl isoxazole; 4- [2-bromo-3- (2-methoxyethoxy) -4-methylthionylbenzoyl] -5-cyclopropylpropyl oxazole; 4- [4-bromo-3- (2-methoxyethoxy) -2-methylsulphonylbenzoyl] -5-cyclopropylpropyl isoxazole; 5-cyclopropyl-4- (2-methylsulphenyl) -3- (2-methoxyethoxy) -benzoyl] -oxazole; 5-cyclopropyl-4- (2-methyl-thionyl) -3- (2-methoxyethoxy) -benzoyl] -isoxazole; or 5-cyclopropyl-4- (2-methylsulphonyl-3- (2-methoxyethoxy) -benzoyl) -isoxazole. A process for the preparation of compounds of the general formula (I) according to claim 1, characterized in that: (a) compounds of general formula (II): (II), wherein R q, R 2, R 3, R 1, R 4 are as defined in claim 1a. B represents a leaving group, reacting with a hydroxyl amine salt; (b) compounds of the general formula (III): (III) in which R 1 is as defined in claim T, are reacted with compounds of general formula (IV): (IV) in which R2, R3, R4 and R5 are as defined in claim 1. (c) compounds of general formula (V): (V), wherein R is as defined in claim 1, and Y represents a carboxy group or a reactive or cyano group thereof, interact with a suitable organometallic substance. A herbicidal composition comprising as an active ingredient a herbicidally effective amount of a 4-benzoyl isoxazole derivative of general formula (I) according to any one of claims 1 to 7 together with an agriculturally acceptable diluent or carrier and / or surfactant:. A method of controlling undesirable vegetation, characterized in that the locus thereof is treated with a herbicidally effective amount of derivatives of 4-benzoylisoxazole of the general formula (I) according to any one of claims 1 to 7. T1. Method according to claim 10, characterized in that the area of inhabitation of the undesirable vegetation is the area used or to be used for cultivation of crop plants and the compounds are used at an application rate of from 0.01 kg to 4.0 kg per 1 ha. LITERATURE 1. European Patent Publication No. 04TQ175