PT96606A - PROCESS FOR THE PREPARATION OF HERBICIDALLY ACTIVE SUBSTITUTED SULFONYLURY DERIVATIVES AND HERBICIDAL COMPOSITIONS THAT CONTAIN THEM - Google Patents

Description

(VII) with a sulfonamide of general formula (IX) e) or reacting a compound of formula (VIII)

(VIII) or a compound of general formula (III) and optionally the transformation of the compound of general formula (I) thus obtained in the respective salt. The invention further relates to the preparation of highly effective and selective herbicidal compositions relative to cultivated plants. The present invention relates to a process for the preparation of substituted, sulfonated acyl sulphonylurea derivatives

of the general formula (I)

Where

R 1 is hydrogen, halogen, C 1 -C 4 alkoxy, haloalkoxy in C 1 -C 4 alkylsulfonyl or a group of the formula COR 2 B 2 denotes hydrogen, C 1 -C 4 alkyl or phenyl; means C1-6 alkyl, C1-6 alkenyl, C1-4 alkoxyalkyl group substituted by one or more halo or halogen atoms; and R 2, independently of one another, denote C ??? alkyl, C ??? alkoxy, halogen, C ??? alkylamino or C ??? alkyl; methine or a nitrogen atom, its salts formed with alkali metals, alkaline earth metals, amines or quaternary ammonium bases, the present invention further relates to a process for the preparation of 4,4-

'/' > '> And herbicidal compositions containing said compounds optionally together with an antidote. The present invention further relates to a process for the preparation of novel compounds of the general formula (I) wherein R 2, R 2, R 2, R 2, R 2, R 2, X and R 2 are as defined above.

In the above definitions (throughout the specification): "alkyl group" is intended to include a straight or branched chain alkyl group, such as methyl, ethyl, propyl, isopropyl, as well as any of the butyl isomeric groups ; " alkoxy group " usually denotes methoxy, ethoxy, propoxy, isopropoxy, or any of the four butoxy isomeric groups, particularly the methoxy, ethoxy, or propoxy group; alkenyl group "may be, for example, an allyl, isopropenyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl, or a pentenyl group, in particular an allyl group or a 4-pentenyl group; - "halogen " in itself or halogen of a halogenoalkoxy group may be fluoro, chloro or bromo, in particular chloro.

Suitable alkali metal or alkaline earth metal hydroxides forming the salts with the compounds of the general formula (I) are potassium, sodium, magnesium or calcium hydroxide, especially sodium and potassium hydroxide.

Suitable amines for the formation of salts include primary, secondary or tertiary amines, such as methylamine, ethylamine, propylamine, isopropylamine, any of the four isomeric butylamines, dimethylamine, diethylamine, isopropylamine,

diisopropylamine, pyrrolidine, piperidine, morpholine, trimethylamine, pyridine, quinoline or isoquinoline, in particular isopropylamine, and diethanolamine.

The quaternary ammonium bases used for the formation of salts are, for example, tetraethylammonium halide, triethylbenzylammonium, trimethylbenzylammonium or any halide moiety of ietrabutylammonium.

The herbicidally active sulfonylurea derivatives are commonly known compounds.

The known sulfonylureas are characterized in that the nitrogen in the 3-position, substituted by a heterocyclic group, contains hydrogen or a C 1 -C 4 alkyl group, preferably a methyl group. or a C1 -C4 alkoxy group, preferably a methoxy group; or a C--C al al alkenyl group, a C--C al alkynyl group, or a C--C alquilo alkyl group. Other substituents have been published in a surprisingly low number of patent descriptive memories.

Sulfonylureas of this type are, for example, described in European Patent Specification No. 152,378 and in Japanese Published Patent Application Nos. J5 8126872 and J6 ... 0078981.

Sulfonylureas exert an excellent herbicidal effect against a large number of monocotyledonous and dicotyledonous weeds, mainly broadleaf and grass weeds. M "Green et al .: Proc.: S. Weed Sci. Soc., 34, 214 (1981), particularly in wheat and barley crops, has the advantage that effective doses are very low (usually 5 to 50 g / hectare). the cultivated plants are damaged to a greater or lesser degree.

used which is advisable for its association with an antidote in cerals and essential in corn crops. European Patent Application No. 127 469 discloses antidotes which may be used after sowing in the pre-emergence period and have the ability to protect wheat and millet from the detrimental effect of sulfonylurea type herbicides. Methyl 2-thiocarbonyl) aminosulfonyl] benzoate and the appropriate ammonium salt, as well as 3 '/ aminoaminocarbonylamino) sulphonyl] -2- or the carboxylated methyl ester.

According to the US Pat. No. 4,434,649, 1,8-naphthalene acid antidote, α- (cyanomethoxyimino) benzeneacetonitrile or 1,1-diallyl dichloroacetamide can be used to give a favorable result in increasing the selectivity of 2-chloro-2- (4-methoxy-6-methyl-1,3,5-triazol-2-yl) aminocarbonylbenzenesulfonamide, 2,5-aichloro- 6-dimethoxypyridin-2-yl) aminocarbonyl] benzenesulfonamide or herbicidally active 2-carbomethoxy-1 H -1,4,6-dimethylpyrimidin-2-yl) aminocarbonylbenzenesulfonamide.

Herbicidal compositions containing a sulfonylurea derivative as the active ingredient, together with gliein derivatives as antidotes, are published in the patent specification Hfingara. 201 445 The object of the present invention was to provide herbicidal compositions containing novel active ingredients having more favorable physical and chemical properties, greater selectivity and less resistance compared to the known sulfonylureas.

In the course of our investigations, compositions containing novel sulfonylurea derivatives of the formula

(I), which are characterized in that the nitrogen atom (nitrogen in the 3-position) of the sulfonylurea group substituted by a hetero-cyclic group contains a group wherein R 2 and R 3 are as defined above were defined above.

It has been found that compositions containing the novel compounds of general formula (I) are particularly useful for weed control since they show an excellent herbicidal effect at an appropriate low dose, are suitably selective in relation to cultivated plants or become selective using known antidotes and, simultaneously, are easily decomposed into the soil.

According to another aspect of the present invention, there is provided a process for the preparation of the novel compounds of formula (I) in inert organic solvents or a mixture thereof. This process comprises a) reacting a isocyanate or isothiocyanate of the general formula (IY)

wherein R1 is as defined above, is derived from an aminopyrimidine or an amino triazine of general formula (III)

wherein R 9 and R 9 are as defined for formula (I), optionally in the presence of a base as catalyst, at a temperature in the range of 0-50 ° C preferably between 20 ° C and 30 ° C, or the reaction of a sulfonylcarbamate derivative of the general formula (?)

(â € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒ (I) E are as defined above at a temperature in the range of 25 to 120 ° C, preferably in the range of 60 ° to 90 ° C; or the reaction of a carbamoyl chloride of the general formula (I)

(VI) wherein R 2, R 2, R 3, and E are as defined above,. -. (I.e. with an alkali metal salt of a sulfonamide of general formula (II) R 1

(II) in which R 1 is as defined for formula (I), in the presence of a base as a catalyst, at a temperature in the range of 1020 to 50 ° C, preferably between 0 ° C and 40 ° F, or the reaction of an N- pyrimidinyl carbamate or R-triazinylcarbamate of the general formula (VII)

r2-ch-or3

000R (VII) ??? 12

in which R 2, R 2, R 2, R 2 and R 1 are as defined above and R 2 denotes a phenyl group with a sulfonamide of the general formula (IX), wherein R 2 is as defined for formula 1) in the presence of a catalytic amount of a base at a temperature of 20-80 ° C, preferably between 2020 and 40 ° C, or (e) reacting a sulfonyl chloride of general formula (VIII)

(I), with an aminopyrimidine or aminotriazine derivative of the general formula (III), in which Rg, R 2, R 3, R 4 and R 5 are as defined above, and cyanates of alkali metals at a temperature of from 20 ° C to 120 ° C, preferably from 60 ° to 90 ° C.

If desired, the compounds of the general formula (I), prepared by the process variants described above, may be converted into their salts with alkali or alkaline earth metal hydroxides, amines or quaternary ammonium halides, for example, by reacting the compound with the appropriate base, in a suitable solvent which is then evaporated,

In the preparation of the compounds of general formula (I), methylene chloride, chloroform, carbon tetrachloride, dichloroethane, tri-13

chloroethane, tetrahydrofuran, acetonitrile, dioxane, benzene, toluene, xylene, chlorobenzene, dimethylformamide, nitromethane, nitroethane, N-methylpyrrolidone, dimethoxyethane, diethyl ether diisopropyl ether, dibutyl ether, hexane, petroleum ether, ethyl acetate, butyl acetate, dibutyl phthalate, as well as mineral and vegetable oils, however the solvents are not restricted to those mentioned above '

In the above process variants the reaction temperature may vary within a wide range, usually between -20 ° C and the boiling point of the solvent used however, it is preferred to react the components at a temperature in the range of from 0 ° C to 90 ° C, in particular between 15 and 45 ° C since this temperature range is useful for also preparing the heat-sensitive derivatives of the general formula (I). the reactions may be carried out in the presence of air, or under an inert gas, for example nitrogen. In order to shorten the reaction time or in order to complete the reaction, only drops of a base should be used as the catalyst.

As catalytically active bases, in particular tertiary amines such as triethylamine, tributylamine, Ν, Ν-dimethylaniline, as well as nitrogen-containing heterocyclic compounds, for example pyridine or 1,4-diazabicyclo [ 2.2.27oethane (DiBCO), although alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide or sodium methoxide, are also useful. Catalysts which are useful in practicing the process variants are not restricted to those mentioned above.

The products prepared using the above process variants,

G may be separated by complete or partial evaporation of the solvent and recrystallization; or by triturating a residue from evaporation with a solvent or a solvent mixture by lightly dissolving the product. If necessary, the obtained compounds may be purified by chromatography on a suitable filler such as aluminum oxide, silica gel or the like.

The herbicidal compositions according to the present invention usually contain the active ingredient of the general formula (I) in an amount of 0.01 to 95% by weight, preferably 2 to 80% by weight in the form of known formulations, for example solutions, emulsions, powders for dusts, suspensions, wettable powders, pastes, soluble powders, granules, suspension concentrates or emulsifiable concentrates natural or synthetic compounds impregnated with the active ingredient or compositions encapsulated in polymeric substances.

The compositions are prepared by mixing and / or grinding the active ingredients with solvent-binding agents and / or carrier agents optionally through the simultaneous use of surfactants and / or dispersing agents as well as of adhesion promoting agents.

Useful solvents are aromatic hydrocarbons, preferably 7 to 12 carbon atoms, for example mixtures of substituted toluene, xylene or naphthalene; chlorinated aliphatic or aromatic hydrocarbonates, preferably chloroethylene, methylene chloride or chlorobenzene; aliphatic hydrocarbons such as cyclohexanone, paraffins, or fractions of mineral oils; vegetable or mineral oils; alcohols, for example, ethanol or ethylene glycol; or their ethers such as ethylene glycol monomethyl ether, ethyl ether; eetones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; strongly polar solvents for 15

Example I-methylpyrrolidone, dimethylformamide, dimethylacetamide, dimethylsulfoxide; esters of phthalic acid, for example, dibutyl phthalate or diolelyl phthalate; epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.

Suitable carriers are inorganic powders such as kaolin, calcite, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, perlite, amorphous silicon dioxide, aluminum oxide, highly dispersed silica, pumice, powder sepiolite, bentonite or sand; organic powders, for example, flour-like powders prepared from plant parts such as cereal stems, coconut shells, as well as barley; various types of starch, processed starch; sugar, for example glucose; powdered or ground synthetic resin, for example, phenol or urea resins. In addition a large number of inorganic or pre-granulated organic materials may be used.

Non-ionic, cationic and / or anionic agents having favorable emulsifying, dispersing and wetting properties may be employed as surfactants. Mixtures of surfactants may also be used. Anionic surfactants are water-soluble soaps, for example sodium and potassium salt, oleic or stearic acid as well as the salts of mixtures of natural fatty acids; however, it is more appropriate to use synthetic surfactants, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulphonate-benzimidazole derivatives or alkyl-arylsulfonates. Mention may be made as examples of the calcium salts of triethanolamine of ligninsulfonic acid, esters of dodecyl sulfuric acid, sulfonic acids prepared from natural fatty acids as well as esters of sulfuric acid and sulphonic acids of fatty alcohol-ethylene oxide adducts, dodecylbenzenesulfonic acid or tributylnaphthalene-

lenosulfonic acid. In addition, phosphates are also suitable, for example, phosphate ester salts of the p-nonylphenyl- (4 " 14) -ethylene oxide adduct. As quaternary surfactants, quaternary ammonium salts containing halogen-substituted lower alkyl groups or a hydroxyl group and / or a benzyl group attached to the quaternary nitrogen may be taken into account and addition to an alkyl group in g Examples of surfactant Examples of such active agents are, for example, stearyltrimethylammonium chloride or benzylbis- (2-chloroethyl) ethylammonium bromide. The nonionic surfactants are mainly polyoxyethylene glycol ethers, polyoxyethylene glycol esters , as well as esters of polyhydric alcohols and their condensation products, nonylphenol-polyethoxyethane, polyglycol ethers of castor oil and adducts of polypropylene-polyethylene oxide, ligninsulfonate, sulfite lye and methylcellulose are, for example, dispersants.

The compositions may contain adhesion promoting agents, for example, carboxymethylcellulose, natural and artificial, powder-like, granule or latex-like polymers, for example polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalin, lecithin or synthetic phospholipids

In addition, the compositions according to the present invention may contain other additives such as stabilizing agents, antifoaming agents, viscosity regulating substances, preservatives, as well as inorganic or organic pigments. may also be incorporated into the compositions according to the invention.

In the present invention, substances which act as synergistic activators and act as antidote.

Also within the scope of the present invention are herbicidal compositions containing known antidotes, such as DKA-24 (N-dichloroacetyl-N-allyl-glycine-N-allylamide), R-25788 (N, N-diallyl-dic loroacetamide), MG-191, (2-dichloromethyl-2-methyl-1,3-dioxolane) TI-35 or CGA-92194. (TI-35 is N- (dichloroacetyl) -hexamethyleneimine, CGA-92194 is N-1,3-dioxolan-2-ylmethoxy) -imino-benzeneacetonitrile.

If desired, the compounds of general formula (I) according to the present invention and the compositions containing them may be used in combination with other agrochemicals,

or attractive plants.

The compositions according to the invention preferably contain 0.01 to 95%, more preferably 2 to 80% by weight of active and antidote ingredients, 5 to 99.9% by weight of liquid or solid carrier, and O to 30% by weight of surfactant 0.1 to 25% by weight of surfactant or other additives.

In compositions which also contain an antidote the proportion of the antidote to the active ingredient may be from 1: 1 to 50: 1. Particularly preferred are the compositions having the following components (percentages given by weight):

1 active ingredient solutions 1 to 30, preferably 5 to 25, 1 to 90, preferably 0 to 85, 1 to 99, preferably 0 to 95%. 2. Emulsifiable concentrate active ingredient 1 to 20%, preferably 5 to 10% surfactant 1 to 30 preferably 5 to 20% liquid carrier 50 to 94%, preferably 70 to 85% 3 '. Wettable ingredient active ingredient 095 to 90 19 preferably 20 to 80 1 surfactant 0.5 to 20 1, preferably 5 to 15 1 solid carrier 5 to 95%, preferably 15 to 90 1

Suspension concentrate Active ingredient 5 to 75%, preferably 10 to 50% Water 20 to 95%, preferably 30 to 80% Surfactant 1 to 40 1, preferably 5 to 20% Active ingredient 0.5 to 10% , preferably 0.5 to 51% to 99%, preferably 95 to 99%, of the solid carrier G-beads active ingredient 0.5 to 30%, preferably 1 to 15% solid carrier 70 to 99%, of preference 85 to 95 $ 19

The compositions according to the present invention may be diluted to an active ingredient concentration of 0.01% by weight with water before use. The compositions may be applied to the site to be treated after or undiluted using standard methods, for example, spraying, dusting, atomizing, spreading, spray, or the ultra low volume method. The compositions containing the novel sulfonyl ureas of the general formula (I) according to the invention have an excellent herbicidal effect against monocotyledones (weeds) and dicotyledons (weeds), annual and perennial. The compositions according to the invention may be applied before sowing or in the pre-emergence or post-emergence period.

When the treatment is carried out prior to the emergence of weeds in the soil without plants, the germinating plants burst and develop into the cotyledon phase (seed-leaf), then their erection stops and they die partially or totally after 3 to 6 weeks. When the treatment is carried out after the emergence of the weeds, the growth of the weeds stops after treatment and the weeds partially or totally die after 1 to 4 weeks. It is a feature of the compositions according to the present invention that they already have an effect on an extraordinarily low applied amount. Depending on the weeds treated the herbicidal effect is very good in doses of 0.01 to 2.0 kg / hectare. It has been found that large-scale crops, for example, wheat, maize, rice, and soybeans were resistant; thus the compositions according to the invention are excellently suitable for the control of annual and perennial monocotyledonous and dicotyledonous weeds, which are difficult to destroy or can not at all be destroyed in the aforementioned crops. Cultivated plants are not restricted to those mentioned above. Depending on the active ingredient employed, they may also

doses of from 0.05 to 2.0 kg / hectare of compositions according to the invention for total weed control will also be used.

A particular embodiment of the sulfonylurea-containing compositions of the general formula (I) as the active ingredient appears to be that after reaching the soil, it rapidly decomposes therein when the compositions are used in the post-emergence, the area of the field employed may be seeded with other plants grown immediately after plant-host harvest or after a short time in comparison with the commercially available sulfonylurea-containing compositions. The preparation and use of the active ingredients / compounds of the general formula (I) and the compositions according to the invention are illustrated in detail in the following non-limiting Examples -

Example 1

Preparation of 3-ethoxyimphl-1- (2-methoxylaminophenylsulfonyl) -3- (4-methoxy-6-methyl-1,3 < 5-triazol-2-yl) -urea (Compound No. 8I

After 0.01 g of DABCO catalyst was added to a solution containing 3.96 g (20 mmol) of 2-ethoxymethylamino-4-methoxy-6-methyl-1,3,5-triazine in 50 ml of diethyl ether , 5.3 g (22 mmol) of 2-methoxycarbonylphenylurea isocyanate dissolved in 20 ml of anhydrous diethyl ether were added dropwise to the above solution at ambient temperature under stirring. The reaction mixture is stirred for 6 hours at the same time.

precipitation of the product begins. The next day, the crystalline precipitate is filtered, washed with a little ether and then dried at room temperature to give 6.5 g (74% yield) of the title product, m.p. 105-106 ° C.

Preparation of 3-Ethylmethyl-1- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea (compound no. 3.96 g (20 mmol) of 2- (ethoxymethyl) amino-4-methoxy-6-methyl-1,3,5-triazine were added to the solution of 6.23 g (20 mmol) (2-chlorophenylsulfonyl) carbamate in 120 ml of anhydrous benzene. The mixture is stirred at 75-8 ° C for 8 hours, then evaporated to dryness. After the residue was recrystallized from diethyl ether, 5.06 g (61%) of the title compound, melting point: 123 ° C.

Preparation of γ-sulfonyl) -3- (ethoxymethyl 6-dimethylpyridin-2-yl) -1- (2-chlorophenyl) (compound n 8 * 2).

4.87 g (20 mmol) of N- (4,6-dimethylpiperidin-2-yl) -H- (ethoxymethyl) carbamoyl chloride dissolved in 10 ml of dimethylformamide are added dropwise into a solution containing 4.27 g (20 mmol) of 2-chlorobenzenesulfonamide sodium salt in 25 ml of anhydrous dimethylformamide, redistilled, at room temperature.

5 to 10-C, while stirring. After addition the mixture is stirred at room temperature for 3 hours and then poured into 250 ml of ice water. The precipitate is filtered off, washed with a little water, dried and then recrystallized from a mixture of ethyl acetate and diethyl ether to give the title product in a yield of 3.34 g (42%). f) pf; 118-119 ° C.

Example 4 Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3-ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) urea (compound n2,6)

After 3.1 g (10 mmol) of phenyl-H- (4,6-dimethylpyrimidin-2-yl) -N- (ethoxymethyl) carbamate (3.1 g, 10 mmol) were added to the solution of 2.15 g (10 mmol) of 2- in tetrahydrofuran (25 ml) and the reaction mixture is stirred at 30 DEG-350 DEG C. for 10 hrs. and then poured into 200 ml of water. After adjusting the pH value to 6.5, the precipitate is filtered, dried and then recrystallized from a mixture of chloroform and hexane to give 1.59 g (37.6%) of the title compound of formula title5 melting point; 124 to 126 ° C

Example 5

Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3-methoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) urea (compound no.5)

A mixture containing 2-methoxycarbonylbenzenesulfonyl chloride (3.times.3 g, 20 mmol), 3.67 g (22 mmol) of 4,6-dimethyl-2 (Diethoxymethyl) aminopyrimidine and 3.24 g (40 mmol) of potassium cyanate in 30 ml of dry acetonitrile. After the precipitated inorganic salt is filtered, the filtrate is evaporated, the residue is again suspended in 30 ml of water, the filtrate is then dried and recrystallized from a mixture of ethyl acetate and diethyl ether to give The title compound was obtained in a yield of 5.4 g (66%) melting point 133 - 135 ° C.

The compounds set forth in Table I are prepared in a similar manner to the Examples above.

Table_I

Compounds of the general formula (I), wherein X = oxygen

Compound is. CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 CH 3 CH 3 CH 3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 Ch3o I 123- 4 5 C00CH3 H ch3 oh3 ch3 OH 133-5 6 C00CH3 H c2h5 CH3 CH0 3 Hu 124-6 7 cooch3 H ch3 ch3 CH30 Έ 112-5 8 cooch3 H0 2H5 ch3 ch3o I 105-6 9 C00CH3 H4 4H9 oh3 ch3o I 100-2

A c

24 ì

Table I (continued)

Compounds of general formula (I), wherein X = oxygen

Compound

N®. % R2 R3 R4 R5 and m.p. C10C00C3Hi-CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CN

Example 6

Preparation of a wettable powder (PM 10)

Heavy components ems

Active ingredient prepared according to

Example 20

Silicate Carrier Agent (Zeotex 444) 80

Siliceous earth (diatomaceous earth) 80

Sodium sulphonate wetting agent (letzer IS) 4

Cresol-formaldehyde sulphonate dispersant (Pispergierm.ittel 1494) 6 Sulphite bleach powder (Borresperse IA) 10

The mixture is crushed in a laboratory ball mill for 30 minutes and then finely ground in an Alpine-63-C type laboratory countertop mill at a rate of 70 ° C. The wettable powder composition thus obtained contains - 25

post n2. Table I as an active ingredient in an amount of 10% by weight. Buoyancy (in 1% concentration)? 86.5 - Wet sieved residue (on a DII 10 sieve)? 0.27

Example 7

Preparation of a wettable powder (PM 50)

Heavy components in? 190 30 50 4 6 10.

Active ingredient prepared according to Example 3

Synthetic Silicate Carrier Agent (Zeotex 444)

Siliceous saw

Aliphatic sodium sulphonate (Retzer IS) Cresol-formaldehyde sulphonate Sulfite bleach powder

The procedure described in Example 6 is followed. The wettable powder composition thus obtained contains the compound No. 20 of Table 1 as the active ingredient in an amount of 50% by weight.

Buoyancy (at a concentration of 1%)% 82,9% ° Solid sieve (on a DIN 100 sieve)? 0.43 26

Example 8

Preparation of a wettable powder (EI 85)

Heavy components in?

Active ingredient prepared according to Example 4

Synthetic silica carrier (Sipernat 50 S)

Oleyl-meilyl-laurate sodium (AREOPOI T plv.)

Crescol-formaldehyde sulphonate

The procedure described in Example 6 is followed. The wettable powder composition thus obtained contains Compound No. 26 of Lab I as an active ingredient in an amount of 85wt.

Plucity (at a concentration of 1%)% 82,9

Wet sieve residue (on a DIN 100 sieve): Oy43 $ »

Example 9

Preparation of an emulsifiable concentrate (01 5) Components heavy;

Active ingredient prepared according to Example 1 5

Xylene 70

Cyclohexanone I5

Calcium Eodecylbenzenesulfonate (Emulsogen IP 400) 8 27

Fatty acid polyglycol ester (Emulsogen EI 400) 2

The active ingredient is dissolved in the mixture of xylene and cyclohexanone under stirring, and 8 g of emulsifying agents Emulsogen IP 400 " as well as 2 g of Emulsogen EI 400 are added. After homogenization the filtrate is filtered, the mixture was stirred. The emulsifiable concentrate thus obtained contains Compound No. 2. 8 of Table I as the active ingredient in an amount of 5 by weight.

Stability of the emulsion (1% concentrate in water CIPAC a and CIPAC D) is stable after 2 hours. ! i

A reversible cremating is observed after 24 hours.

Example 10

Preparation of the sprinkler stand (51)

Heavy components in? g

Talc 20

Silicate (Sipernat 50 S) 30

Active ingredient prepared according to Example 50 ground limestone (M 10) 900.

The mixture composed of the active ingredient prepared according to Example 5, the synthetic silicate carrier and the talc is crushed into a laboratory bean mill, then ground into fine particles in a laboratory or laboratory mill of the Alpine type 63 0. Grain with limestone is homogenized * - 28

ground in a laboratory powder mixer. The dusting powder thus obtained contains Compound No. 2. 5 of Table I as the active ingredient in an amount of 5% by weight.

Sieve residue (on a 100 DIST sieve), 0.12%.

Example 11

Preparation of a suspension concentrate (5 PW)

Active ingredients prepared according to Example 2 10

Sunflower oil 168

Organophilic Bentonite (Ivegel) 2

Polyethylene alkyl ether, polyoxyethylene castor oil, ethoxylated fatty acids and sodium sulfosuccinate (Sorpol 3815) 20.)

The active ingredient, sunflower oil, organophilic bentonite (Ivegel) and Sorpol 3815® emulsifying agent are weighed in a laboratory bead mill, together with 65% by volume glass bead loading 1.0 to 1.5 mm diameter at 775 rpm for 30 minutes. The suspension concentrate thus obtained contains Compound No. 4 of Table I as the active ingredient in an amount of 5% by weight.

Stability (1% water concentrate CIPAC and CIPAC D) is stable after 30 minutes. Example 12

(I.e.

Preparation of a suspension concentrate (40 μM)

Active ingredients prepared according to Example 1 Synthetic Silicate (Zeolex 444) Sodium Oleyl Methyl Tauride (Arkopon 2 plv.) Phenylphenyl Polyglycol ether (Arkopal I 100) 2% Xanthan gum solution (Kelzen S) Water £ 80 6 4 10 10 80

80 g of active ingredient prepared according to Example 1, synthetic sodium silicate (Zeolex 444), sodium oleyl methyl tauride (Arkopon 2), and wetting agent, nonylphenyl polyglycol ether dispersant (Arkopal H 100), as well as 80 g of water. After homogenizing, the suspension concentrate was ground with 70æ by volume loading of glass beads 1.0 to 1.5 mm in diameter for 30 minutes. After grinding and separating the filler, the mixture is homogenized with 20 g of a 21 g xanthan gum solution (Kelzen S) in Ultura turrax under gentle agitation. The suspension concentrate thus prepared contains Compound No. 8 of Table I as the active ingredient in an amount of 40% by weight.

Plutoability (in concentration of 11) i 97.3 1 °

Granulometry (less than 10 g)% 91.6 30

Example 13

Preparation of water-dispersible granules GD® 75)

Heavy components ems g

Compound is.3 of Table I as

Active ingredient 375

Synthetic Silicate Carrier 55

Polyvinylpyrrolidone (product K 30 from BASF) 20

Alkylphenol-ether-phosphate (Ailax 5330 ICI product) 30

Mixture of polyalkylene glycol ether and polymethylene ether alkyl ether (Atlox 4896 product of 101) Water 180.)

375 g of Compound 12.3 of Table I is pre-crushed as active ingredient with 55 g of synthetic silicate carrier, then the fine particulate mixture is ground into a Alpine 63-C type contraplex grinder at a rate of 80 The granulation liquid is prepared by dissolving 20 g of polyvinylpyrrolidone, 30 g of alkyl phenol ether phosphate and 20 g of a mixture of polyalkylene glycol ether and polymethylene alkyl ether in 180 ml of water. The ground mix is introduced into an operation granulation apparatus in discontinuous loads of the PPG type 0.5 (periodically driven) with flowing atomization and leads to a fluidized state by regulating the inlet of the air stream with a temperature 60-65 ° C. When the inlet temperature reaches 30 ° C, the granulating liquid is evaporated under a pressure of 1.5 bar and the air flow is increased, depending on the growth of the particles. After the granulation liquid has been introduced, the

the drying is continued until the outlet temperature reaches wd j and cs »38 ° σ.

The granules thus prepared contain the HS Compound. 3 of Table I as the active ingredient in an amount of 75% by weight.

Buoyancy (at a concentration of 1 # after 30 minutes)? 93.7%.

Granulometry between 0.2 and 1 mm; at least 75 °

Example 14

Preparation of dispersible granules in water (GD 25)

Heavy components in; g

Compound iía. 7 of Table I as the active ingredient 125

Synthetic Silicate Carrier 250

Maltodextrin Binding Agent 75

Ligninosulfonate (Sorpol 9 13 47 K product of Toko) 30

Polyoxyarylene polyalkylarylphenyl ether sulfonate (Sorpol 5096 Toko product) 20.

Weigh in a laboratory ball mill the Composite in. 7 of Table I as the active ingredient, the synthetic silicate carrier, the maltodextrin binding agent as well as the lignin sulphonate (Sorpol 90 47 E product of Toko) and the polyoxyethylenated polyalkylarylphenyl ether sulfate surfactant ( Sorpol 5096 Toko product). After milling for 30 minutes, the powder mixture was ground to fine particles 32.

in a Alpine type 63-C counter-type mill. The grain is introduced into a PPG-0.5 discontinuous charge-operated fluidization apparatus (periodically driven, with flowing atomization and brought to a fluidized state by adjusting the air stream to an inlet temperature of about 60 DEG C. The granulation is carried out by atomized water until the exit temperature reaches the B8 at 30 DEG C. After the desired granuometry of about 0.5 mm is reached, the water is atomized and the drying is continued until the outlet temperature reaches 36 to 38 ° C.

The granules thus prepared contain Compound No. 2. 7 as an active ingredient in an amount of 25% by weight.

Plutuality (at a concentration of 1% after 30 minutes) t 91 * 85

Granulometry between 0.2 and 1.0 mm; at least 95 faith *

Example 15

Preparation of a suspension concentrate (FW 14.5)

Heavy components in; g

Compound No. 2. 8 of ligne I as active ingredient 2 DIC-24 (1-dichloroacetyl-1-allyl-glycine l8-allylamide) as antidote 12.5

Zeolex 444 Carrier Agent 11.6

Kanoethyleneglycol 15

Wetting Agent Arkopon T 3

Arkopol 1-090 dispersant agent (nonylphenyl polyglycol ether) 39.9 33 Γ. i

Water 39.92% by weight of xanthan gum solution as thickening agent 10.

Prepared as described in Example 12, the suspension concentrate containing the active ingredient (Compound No. 8 of Table I) and DKA-24 antidote in a total amount of 14.5% by weight, in a weight ratio of 1: 6.25.

Example -16

Preparation of a suspension concentrate (1 × W 27.0)

Heavy components in: g

Compound ns. 8 of Table I as the active ingredient - 2 R-25788 (1,1-diallyl-dichloroacetamide) as the antidote 25

Zeolex 444 Carrier 5

Monoethylene glycol 10

Arkopon wetting agent Ϊ 2.5

Arkopol dispersing agent 1-090 5.5 Water 42 2 wt. Xanthan gum solution as thickening agent 8.

The procedure described in Example 12 for the suspension concentrate containing the active ingredient (Compound No. 8 of Table I) and the antidote R-25788 in a total amount of 27% by weight in a weight ratio of 1% 12.5. 34 34

Example 17

Preparation of a wettable powder (PI 20.25)

Heavy components in; g

Compound 12. 4 of lamella I as the active ingredient 1.5 Â ± B-67 (N-chloroacetyl-1-oza-4-azaspiro [4,5] decanane) as antidote 18.75

Zeolex 444 Carrier 34 * 75

Silica saw (diatoms) 33 * 0

Wetting agent Fetzer IS 3

Dispersing agent Disperglermittel 1494 4 Sulfite bleach powder as dispersing agent The process described in Example 6 was followed to obtain a wettable powder composition containing the active ingredient (No. 4 of Sabela 1) and the anti-duct AB-67 in total amount of 20.25% by weight in a weight ratio of 1; 32.5.

Example 18

Preparation of dispersible granules in water (G-M 13,5)

Heavy components ems g

Compound No. 2. 6 of Sabela I as active ingredient 1 CG-A-92194 [1,3] dioxolan-2-ylmethoxy) -imino-benzene-acetonitrile as an antidote 12.5

Synthetic silicate carrier 61.5 35 Moltodextrin binder

Ligninosulfonate (Sorpol 90 47 K) 15 6

Polyoxyethylenated polyalkylarylphenyl ether polyoxyethylene (Sorpol 5096) 4.

The procedure described in Example 14 is followed to provide water dispersible granules containing the active ingredient (compound No. 6 of Table I) and the antidote (DGA-92194) in a total amount of 13.5% by weight in a proportion in weight ratio of 1 x 12.5. Example 19

Preparation of a wettable powder (MW 51.2)

Heavy components ems g

Compound No. 2 of Table I as active ingredient 20.4 as antidote 31.2

Zeolex 444 Carrier Agent 14.4

Silicone carrier 24,4

Wetting agent IS 2

Cresol-formaldehyde 3 Sulfonate

Sulphite bleach powder dispersing agent 5.

The procedure described in Example 6 is followed to provide a wettable powder composition containing the active ingredient (Compound No. 2, Table I) and the antidote (MA-24) in a total amount of 51.2% by weight in weight ratio of 1: 1.56. Example 20

Preparation of a wettable powder (MW 24 * 75)

Heavy emi &

Compound No. 2 of Table I as active ingredient 16-191 (2-dichloromethyl-2 ', 3'-methyl-1,3-dioxolane) as the antidote Zeolex vehicle agent 444 silica earth carrier Agent mulling agent Netzer IS i Dispersing agent Dispergiermittel 1494 Sulphite bleach powder dispersing agent 6 18 * 75 33 32 * 25 2 3 5

The procedure described in Example 6 is followed to give a wettable powder composition containing the active ingredient (Compound No. 2 of Table I) and the antidote (MG-191) in a total amount of 24 * 75% by weight * in a proportion by weight of 1? 3,125.

Example 21 Preparation of a powder for sprinkling (D5 * 2)

Heavy components ems g Compound n2. 5 of Table I as active ingredient 2 AD-67 as antidote 50 Talc 19 f) 37

Synthetic silioate carrier (Sipernat 50 S) Ground limestone (type M-10) 29 900

The procedure described in Example 10 is followed to give a powder containing the active ingredient (Compound No. 5) and the antidote (AD-67) in a total amount of 5.2% in weight ratio of 1: 25.

Example 22

Preparation of a wettable powder (MW 21) JL-1 20 30 39 * 5 3 2 4 * 5

Heavy components in;

Compound Sis. 6 of Sabela I as active ingredient ΏΕΑ-24 as antidote

Zeolex 4-44 Carrier

Silicone carrier

Dispersing agent dispergiermittel 1494

Wetting agent IS letzer IS Sulphite bleach powder

The procedure described in Example 6 is followed to give a wettable powder containing the active ingredient (Compound No. 6 of La Belle I) and the antidote (ΌΚΑ-24) in a total amount of 21% by weight in a proportion in weight of 1 s 20. //

38

23

Example

Preparation of a powder for sprinkling (D 6) 10 50 15 25 900

Heavy components ems

Compound 4 of Table I as active ingredient DKA-24 as antidote

Baby powder

Synthetic silioate carrier (Sipernat 5Q S)

Molasses limestone (type M 10)

The procedure described in Example 10 is followed to give a powdered powder composition containing the active ingredient (Compound I.4 of Table I) and the antidote (DKA-24) in a total amount of weight β in a weight ratio of 1 j 5.

Example 24

Preparation of a suspension concentrate (E ¥ 22)

Heavy components ems g

Compound No. 5 of Table 1 as active ingredient 2 DKA-24 as antidote 20

Zeolex 444 Carrier Agent 6

Molting agent Arlcopon T 4

Molar agent ârkopol M-100 10 2 wt% xanthan gum solution as thickening agent 10 Water 48 39

The procedure described in Example 12 is followed to give a suspension concentrate containing the active ingredient (Compound No. 5 of Table I) and the antidote (DKA-24) in a total amount of 22% by weight, in a weight ratio of 1 ; 10,

Example 25

Test in (effect on plants born);

The seeds of the test plants were seeded into a mixture containing 1/3 part sand, 1/3 part clay and 1/3 part soil of "flower chernozem" placed in plastic containers of 200 ml containing 4 holes in the bottom '

After sowing, the soil and small plants, respectively, were sprayed daily at a temperature of 20 to 26 ° C under additional natural light and a 4 hours illumination. The PM 10 composition prepared from the compounds no. s, 3, 5, 6, 7 and 8, respectively from Table I according to Example 6, using 1000 liters per hectare of water under a pressure of 4 bars on 2-4 leaves plants using a greenhouse sprayer »

The damage (losses) of the test plants were evaluated in 2i and 4. weeks after spraying. Damage to the various test plants is given as a percentage; 0% means no damage and 100 fo means complete destruction.

The results are summarized in Table II. It can be seen that the compositions according to the present invention have a good herbicidal effect and a selectivity favorable to the cultivated plants. The compounds no. 3, 7 and 8 proved to be particularly effective.

In the first column of Table II and the following Tables, Roman numeral I refers to Table I and the Arabic numeral refers to the compound number in Table I.

Table II

It is made of

OOM- pos- Dose Deviation of test plants ($) to (in

Table g / ha DRYS STEM EGHC GALA ΜΑΤΙ ZEAM HSLA GLIM TRX1 I) 1/3 270 30 100 80 100 100 20 100 80 0 90 0 100 60 80 100 0 100 30 0 30. Ό 100 0 40 90 0 40 30 0 10 0 100 0 30 30 0 0 0 0 1/5 270 100 100 100 100 100 100 100 100 100 1/6 270 90 100 100 35 70 100 100 80 100 90 80 100 100 30 50 90 100 50 90 1/7 270 10 100 100 60 100 10 100 70 0 90 10 100 100 50 100 10 100 60 0 30 0 100 20 25 90 0 40 0 0 10 0 100 0 0 30 0 40 0 0 1 / 8 270 20 100 100 70 100 100 100 90 0 90 20 100 90 50 100 20 100 60 0 30 0 100 30 40 90 10 100 40 0 10 0 100 0 30 90 0 70 10 0

Abbreviations in Table II% ORYS Oryza sativa STEM Stellaria media EGHC Ecbinochloa c.g. GAIA Galium aparine ΜΑΤΙ Matricana inodor ZEAM Zea mays HELA Helianthus annus GLIM Glycine Max TRIE Sriticum aesticum 41 £ u 26

Example

Pre-emergence plant scam test;

The seeds of the test plants were seeded in three replicates in a soil of flowers of an impermeable medium, placed in a 7 cm high perforated bottom paper carton with a base area of 200 cm. The separate treatment boxes were placed in plastic trays equipped with a wetting coating. After sowing, prior to emergence of the plants, the prepared PI composition 10 of the compound no. 7 of Table I according to Example 6, with an amount of water corresponding to 1200 liters per hectare on the soil surface in the boxes using a greenhouse micropulver. Ensure the addition of water keeps the wet coating in a wet state. The experiment was carried out at a temperature between 20 and 28 ° C under natural light added with a 4 hour illumination. The herbicidal effect of compound No. 7 of Table I was evaluated at 4Â ° C. and 6 weeks after spraying. The results are summarized in Table III.

Table III pre-emergency effect

Compound Destruction of test plants ($) 12. (in Dose Solanum Digitaria Table I) g / ha migrran adans ECHC STEM TRIE 1/7 250 70 50 20 100 0 1000 100 60 40 100 0 42

Example 27 grown in plant height chamber

400 g were weighed for each field surface soil vessel (pH value 6.5, permeability 50 and humus content 1.4 g) in cultured plastic vessels each with 0, 8

The surface dm leveled with PVC sheet. Ten seeds of maize Pi-3737, 100 sunflower seeds " IRSG ", 50 sorghum seeds SA-114 and 1 g of red kidney corn were seeded in this soil.

After the seeds were covered with 100 g of soil, the treatments were carried out. In the course of these treatments, control compositions were applied to four replicates at doses of 10, 20, 40, 80, 160, or 320 g per hectare, respectively, of dispersible granules in water (GDA 75) prepared according to Example 13 of compounds ns2. 2, 4, 5, 6 and 8, respectively, as well as Ally, Tell, Granstar, Glean, Sogran and SL-950 respectively. The treated soil surface was again coated with an additional 100 g of soil in each vase.

The pots were grown in chambers for plant culture, sprayed daily until they reached their water absorption capacity, and were grown under HGMP / D 400 lamps replacing sunlight with a daily illumination period of 16 hours. The experiment was evaluated at 102. dis after the sowing at which the green height of sunflower, sorghum and millet was determined. The results obtained are summarized in Table IV with the designation " Seeding 1 " "

Seeds of corn, gerasol and maize were repeated 43

6 times in the soil of the evaluated experiment. The results of evaluation of the latter experiments are given in Tables 1 to II, with the designations "Seed" II, III, ΓΥ, Y, YIM.

Between sowing I until the YI sowing evaluation, it was 76 days. i 44

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Herbicide activity test in a field experiment on a winter wheat crop:

An experiment was carried out on the control of post-emergence herbs in winter wheat, in plots of 10 m each, near the Sebes-Kórós river.

The test was carried out on a type of meadow clay having a pH value of 6.3 containing 3.4% of organic material used as a winter wheat green crop. The seeds were sown on 24 October on a well-processed dry seed bed at a depth of 6 to 7 cm with a distance between the gutters formed by the direct seeding. The test was post-emerged only on April 20. The species of weeds and their state of development. at the time of treatment they were: mint-love (Galium aparine, abbreviated GALAP) in the state of 4 to 6 leaves; (Lamium purpureum, LAMPU) (Lamiun amplexicaule) silky nettle at the flowering stage, veronica of the meadows (Veronica arvensis, VERAR) at bud period, at the beginning of flowering; molar herb (Fumaria offícinalis, FUMOF) at the 6-leaf stage; morugem vulgaris (Stellaria, médiâ * íÉ STEME) at the flowering stage; spore (Consolida orientalis, CONOR) with 10 cm of height, at the preiódo of stem formation; catassol (Chenopodi-an album, CHEAL) in the s t: ád io-dç &gt; 2 to 6 sheets; Bumblebee (Bilderdyckia convolvulus, BILCO) at 2 to 3 bubbles. In order to establish the experiment, a propane-butane gas pressure plotting machine was used. Doses of 10 to 80 g of active ingredients per hectare have been applied. 4,5,6 and 8, respectively, of Table I in 500 liters per hectare of spray liquid in the form of a suspension concentrate

A ** 58 are FV / 5 formulated according to Example 11. The same doses of Achieve were used for comparison. 75 DF and Granstar 75 DF, respectively.

The herbicidal and phytotoxic effects of the treatments, carried out under these tests, were evaluated using a. scale from 0 (inactive) to 100 (total death). These evaluations were performed 4 times (in 27 of ibril, 4 of May, 25 of May and 18 of June) in the vegetative period following the treatment, p

measuring the number of spikes (portion / m), length of spike (in) and weight of 1000 grains (g). The results which are the mean values of 4 replicates, are summarized in Tables X to XYI. 59.

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Oo

Table XIII

H '• • • • • • • • • • • • • • • • •

C5 O 0) 5d β 5T Ο · Η p) to ω a á>

H 5} · O σ d-H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H VD tH ΓΟ CA O Cví m ω ΟΛ CM CM CT «H o OOO OOO o o o o o c c c c c c c c c c c c c c c c c c c HO tn O o rH H Ή rH CM CM CM o LA ca rH rH LA fA OH rH CM CM H CM RO m ω O LA H σ »O LTV H rH O« H CM rH OO m CO> CM CM CM CM

β β H 0 &gt; 9 0 H &gt; € &gt; H H H H H H H H H H H H O H E H H H H H H H H H H H H H H H H H H H H H H H H H H H

I

Ϊabela XIV φ cá cá cá cá O O O O +

Pi

0 U P

P O 8 8 g g O »O O * H Pi Ha ω l> A Ω 0

43 cS P ro o 43a 0

0 0 0 O O O Ο ro VO CM cofoO vo σ &gt; H0 ro c0 ω H &quot; = a &quot; σ &gt; σν H fO HO 0 o CM VO o ο OO 0 0 OO 0 ο MD VO ω ro O &lt; \ J v 1 The CM ω S IA H νο OO 0 OOH * 3 * ο H LO CM ΙΠ vo σ Ο ro ro> E &gt; H ro 00 σο O &quot; 53 · VD H m m O H- 00 CO fO σ &gt; σ »ro ω O ^ r o νο O CM £> a \ O CM σν 0V ω ω CM o m O νο H fO ω σ * H * 3 * ΟΛ σι 0 Ο Η 9 &gt; »Q Η S Ι &gt; Η Η η Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ. Ο ο Ρ Ρ 68) gabriel XIV (continued) 03 & O? R? O?

tr

O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O

OOO O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O La O ca o ta R os R R RR R ra R Os Os Os O O O O O ca ca ca ca ca ca ca ca ca ca ca ca ca R R R R R R R R R

9H-NMR (DMSO-d6):? or H H H 9 H H H H H H H

O O 100 100 100 100 81 - 0 0 100 and 9Ei

R4a

ι 69) fi

SaMJLa

D-53 • d-4 • H O

M o o * P o • Η P p H H

or P • H © P P «4

The salt is filtered off and the residue is evaporated to dryness. EH < 1, 2, 3, 4, 5, 6, 7, 8

O o o o H LA OJ 0 &quot; &gt; H Ή JA 00 CA Α VD 1-'ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ »» »» »» »» »» »» »» »» »» »» »» » VD A-

The O-O-O-O-O-O-O-O-O-O-O-

rO -sS · VD 00 I cov Ο Γ Γ Γ Γ - - - - - - Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ.

Lf \ p_ | 18 s 91 16 38 82 06 O and 0 and H »H e s H M H 0 JH H> H H H H H H H

o H C? J <4? EH P4 with 2 p a

why p

Sj ci? LA A-LA A-70) gabriel XV (continuation) α &gt; «D K &gt; or H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H The invention relates to a process for the preparation of a compound of formula (I) wherein the compound of formula (I): wherein R 1 is as defined in formula (I). The title compound was prepared from the title compound as a colorless oil. H rd • Φ u Q) t => & and O O fd P Hl CM rd ω • H a>  € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒâ € ƒ- cd 0 or • H a H Pi O H H a H M H ω P EH ¢ 8 © ¢ 8 83 í! O O-3t p 63 CFR p h ω cd to P fd cd m p 12 ri cS LA & ! &gt; EH you »

The ri 'LA OO iH HO LA σ »LA ω o cr» H VO cr »H« ftf ≤ d ω v 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 00 03 The IAEA M I &gt; & & & & & & & & & & & & & & & & & & & & & & & & & LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA. 03> 0> 0 0 H &gt; M and H M H H H H O ω 9 -P Fr 03 P LA & T the

71 &gt; m is 0) m is Pi

ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN α α α α α It's me H5! iH ω JO here M a a * tá tá tá tá P! dl 03 <1) 1 PS | m? sc? p? &gt; '. M.p. 110-130Â ° C. (A) (b) and (b). to Pi

O ffi ©

§ § \ \ \ \ Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η

CA CM Aω co (X)

CA ω CNJ a tá 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN CN ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ ΙΑ 03 © 630 7.8 22.0 4-0.6 © here Ο ο Ο ο Ο m Λ 8 Η <λ! • r r cá cá cá cá cá Ο tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá tá amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo amo 5 amo amo * oω 40 72) gabela XVI (continuation)

02 O m o 4 m m

Q)

H 00 H CM c- «ςτ σ ≥ 5¾ Ci <A is> λ and * CM CM &lt; 5 $ &quot; m ΓΟ «« á á á 4 4 4 MB MB MB MB 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4. (1) (1) (1) (1) (1) (1) (1) (1) (¾ Η Η Η Η Η Η Η U U U U U U ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι 3 and 4 are the same as those of the present invention. The present invention relates to a process for the preparation of a compound of the formula: ## STR1 ##

O H

The CM O M · Oω o «Η

The CM

The hollow

O H

S s H P P P P P C P P P P P P P P P P P

The h

They achieve 75 73 &gt; 0 -> j / f -

02 or i3H

(x), where x f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f f The compound of the formula

Or ω · = φ Γ * &quot; ·? the Î ± and β and the Î ± and β H and the β-Î ±

(a) Pt * H at Pt &lt; 3% &lt; A &lt; tb &gt; ω-CO-co-CMM at oF-1

»» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» »» CM NÍ- 00 H CM 'Μ * ω Ω ws th «a &gt; C 3 H 3 O 2 O 3 H 2 O 3 H 2 O 3 H 2 O 3 H 2 O cS 43 3 3 cS © P = t 03 Ρπ 02 Ρη © Ph • fr »1 P FH Fh d Ω d Ω ≤ 3 Ω d Ω cg * 50 * 30 * 10 3 3 © 3 I4 ooouu Fh U! 74/3 &quot; / Λλ

p: L

From the results illustrated in Labels I to XVI, it can be clearly seen that a difference appears between the efficacy of the compositions according to the invention and those of the commercially available compositions used for comparison. Compositions containing the compounds I2s. 4 and 8 of labela I proved to be highly effective by late post-emergence treatments in weeds developed from extremely strong infestations. The selectivity to the cultivated plants of both compounds is also favorable. Due to its high phytotoxicity as well as to its weak, possibly inactive, weed control action, the herbicidal compositions containing the compounds no. 5 and 6 of Labela I are not suitable for the control of weeds in the winter wheat crop.

Example 29

Investigation of the antidote composition effect on plants grown in a plant culture chamber

40 g, for each vessel, of field surface soil (having a pH value of 6.5 * permeability of 50 and ha-mus content of 1.4 5) were weighed into plastic culture vessels each one with 0.8 p dm of surface level with PVG sheet. Ten seeds of maize Pi-3737 and 10 striped ttIREGM sunflower seeds were sown in this soil. The seeds were covered with 100 g of soil, after which the treatments were carried out in 4 replicates. In the course of these treatments doses of 20 to 160 g per hectare of active ingredients were applied. 2, 4, 5, 6, or 8 respectively of Eabela I together with 250-500 g per hectare of the antigens DEA-24, ÂD-67, R-25788, MG-191 or CGA-92194 respectively in the form of formulated compositions of

according to Examples 15 to 21. The treated soil surface was covered with an additional 100 g of soil in each vessel.

The pots were placed in a plant culture chamber and cultured with a daily illumination period of 16 hours. The plants were sprayed daily until they reached their water absorption capacity. The experiment was evaluated by measuring (measuring) shoot length and green weight at 13a. day after treatment. The results are summarized in letters XVII to XIX. 76)

SaTbela XTIJ

0 t cd P 03 Pt P * • p &lt; a P 0 O CM 0 IA ω Ο P * P THE CAr P * P IA Ο t &gt; νο CA 0- vo M 8 < 0 C? The Η O IA νο t &gt; P CA p- t O CM EP 00 t CA t Pt -PO PS O CM r0 0 1Α O IA · e- • HOHA 00 ω 0- P LA o- ω ca H H P P ω * è O o IA IA CM rO CM CA A 03 0) CM ω 0 n i> VO-P tl0 The cd 02 • P d O in O C- ω ω The CM p- VO OOO no 00 IA H ca p · P C- CA c- Pt t o r ω ia § P CM O 0 P 8 IA 0 VO o- VO CM P P4 0 ta to CM P <ac A CA ο- ω O 0 A CQ 0 POO P- • H +3 0 O VO VO O 0 ω CM a PS P IA IA IA P o- 00 ω r- | VQ o S βΗ 1 is f • O • • • • C C C C C C C C C C Φ Φ Φ g g g g g g g g g g g g g g g g g g g g g g g g. t is CM--------------------------------& & & & & & & & &. MB, P 0 C O O 0) IA P m OPP p tá P CM CA 00 IA P VO CA o • F PJ 0) cd 05 -P CM a s3 \ 0 CA OP CM VO • H ω m ω IA CM P VO LA S &gt; Φ P P is 0 0 ω &gt; ω Pt • H if 02 δΟ • P ω 0 fl O o 0 O 0 OO ta PP cd P * p- CM VO CM p- ω PP ra 0 P ps 3 Φ cd Pi 00 p- VO CM LTV δΟ -P \ H-NMR (CDCl3):?

(I.e.

(L Saneia XVIII © H-uP st os O Φ CA Ο Ο Ο ca ο ο ο ο ο ο ο ο ο ο O O O O ο ο O O O O O O O O O O O O O O ΓΟ © © © © © © © © © © © © V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V V. &gt; ΓΟ ω ο 02 02 02 02 Pi Pi Pi Pi Pi Pi Pi Pi Pi Pi Pi Pi LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA LA ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ ΓΟ LA LA LA O O O O O O O O O O O O O O ΙΑ Ο C- P J4 to co LA &lt; a CA γΟ &lt; α νο ω ω -PH i &gt; H Η * * * * * * * CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM Η Η Η Η Η Η Η Η ω Η C-CM Ο a «H LA CA CA CA νο οο il © © © 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 CA CA CA CA CA P P P P P P P P P P ε- oo «d 02 ooo 60 rd O -P rd O rO si O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O Hr-1 CM • H S4-P8 60 to P) VO Ε- -3-3 &gt; 0 5 © P CM 00 Ο Μ · CA Μ Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ο Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ Ρ SS Ν © 60 1 © • Η m rd ο © η 60 O • P © ω

O

O

The CM

The vo tH

the CM O 'φ 4® © n e-i ω ^ τ νο CM ΙΑ \\' ns- \\ Η Η Η Η Η

9 U O P o P

Development of the green weight of the sunflower, IREGJ 'listradosoD the effect of the treatments o Κβ σ &gt; O O H o ω-γΟ ΓΟ 'd * CM H CM o ca LA LA Γ- D- 00 CD h i • P O * -! γο <Η Η Ο tí O LO. tn CA νο ω νο OOO CM ω The CM or O ιη la θ '* Ο tn o H LA σ * ω LA 0, SP' ΐ O V0 ΚΩ -P CÍ5 IA tn O Η ο CA ιη t η CM H H V Η Κ η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η η CM Γ- ω LA ω C- ΚΩ -Η -PO mm O tf O CM ω Ε- 00 ο .¾ c- M) MD J tn C- ω ΚΩ ω tr ιη o ο ο R LA «H ^ * Ο ο and Γ-CM-ω Κ Κ Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η Η. -T t t t t Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ Κ-Κ - • Η ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ra ο ο d CM Η CM mo CM P CM C CM η η η η η η η η η η η η η η η η η η • • • • • • • • • • • • • • • • • •

Testing the effect of anti-doped compositions on plants grown in a άβ-plant

400 g of surface field soil (with a pH value of 6.5 * permeability of 50 and 1.4 μm content) were weighed into pots of culture plastic each with P 0 * 8 dm of surface * leveled with P? C leaves. Ten seeds of maize Pi-3747 and 50 seeds of sorghum SA-114 were seeded in this soil. The seeds were covered with 100 g of soil, then the treatments were carried out in 4 replicates. In the course of these treatments doses of 20, 40, or 80 were respectably g per hectare of the compounds. 2, 4 * 5, 6, or 8, respectively from Table I, together with 400 g per hectare of antidote DIA-24s in the form of compositions formulated according to Examples 22 to 24. The same doses of Glean Granstar, Ally or Te 11, respectively, together with the antigen DICA-245 for comparison. The surface of the sprayed soil was again coated with an additional 100 g of soil in each well.

The pots were placed in a culture chamber and cultured with a daily illumination period of 16 hours. The plants were sprayed daily until they reached their water absorption capacity. The experiment was evaluated by measuring (measuring) the shoot length and the green weight in the 12s. day after treatment. The results obtained are summarized in Table XX. 80 ° C). The composition of the present invention is shown in Table 1 below. The composition of the present invention is shown in the following table in which: ## EQU1 ## wherein R 1 is H, <5 The ω od R &quot; M &quot; 54 ω 4 "l &gt; the ta ω R cq> R? £ t0 4 | OWOR * sd * 4- or 8 d A1 • HR or H * d> d • H © CtO a? 4 or? 50 or • P odd r • H • H • P a O o o P P P) d R ω ω ω a R -P -P -P -P -P a a a a a a a a a • • • • • • • • • •

The

The term "CM" is defined as "CM" or "CM". H

Π Γ ca ca ca ca ca Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ Γ ΟΟ ΟΟ ΟΟ ΟΟ ΟΟ ΟΟ &lt; Α rn νο σ Ο σ ΓΟ ο Ε &gt; LA νο ΙΑ · * $ · CM (Α

VO CM ί &gt; ο Η ΙΑ νο! Α ω ω 00 νο σ »ω νο ΙΑ CM ο cn Η C- <Α Η ω Ο C- ΙΑ m νο CM Η Η Ή Ή Ο Ο Ο Ο Ο Ο Ο Ο CM 00 CM here - οο CM ch 00 00 νο Η Η Η

81 A / 1a) 14ora ta &gt;

&lt; 3 &gt; <D P gabela XX (continuation the rd Φ «« «« «« «« «« «« «« «« «Φ Φ Φ Φ Φ Φ H H H H H H H H H H H H H H H H H H H CsO or rJ Hl CD C- O O 'Φ LTV in-d---tr tr MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD MD A A A A A A * HH oo ta m VO Φ I-S rd CM bQ Φ -4 O MO Φ Φ Φ Φ---------- + cn HH r- ve 00 HHH om Φ P4 o rd O p φ o to rd aoo I o • H -P ud dl r Q η η η η η η η η ώ ώ 00 00 00 o o o o o o ; Γ Γ Φ Φ Φ Φ Φ Φ Φ Φ Φ Φ Φ Φ & & & & & & & & & & & & & & & & & & & & & & & & & & & &. H 4 in H 2 O 3, O Φ P P P P P CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00

'S H

&lt; / RTI &gt; Φ H to 82

THE RIGHT OF THE FUTURE. (d) D (m) d H (m) d (d) the BQ CM ω d VD ο R Λ Λ Λ Λ M) / / / CM CM CM CM CM f f f f f f f f f f f f f f f f f f f f f f f f Nj od ·> 4 • d cd ω cd φ A <tí · = Φ \ H d CM «) 0 φ 8 R &gt; = a3 The cd M o ΕΊ o R d · VD <B C-0> + R o 8 o rijá Φ t &gt; the d • HO dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt dt • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • O o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o

m vo H n H ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι ι t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- t- H \ \ \ \ \ CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM CM H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H &lt; d E-i

Claims (1)

83 83 RIIVIEDICAOOES lâ. - A process for the preparation of sulphonylurea derivatives of the general formula (I) in which R4 is hydrogen, halogen, C1 -C4 alkoxy, haloalkoxy in C1-6 alkylsulfonyl, or a group of the formula wherein R4 is hydrogen, C1 -C4 alkyl, Og, C -C-C al alkenyl, CC-C ale alkoxy-alkyl, C alquilo-C alquilo alkyl substituted by one or more halogen atoms or R e and R, independently of one another are C alquilo-C alquilo alkyl; C1 -C4 alkyl, halogen, C1 -C4 alkylamino, C1 -C4 alkylamino, piperazinyl or morpholinyl group means oxygen or sulfur and is a methine group or a nitrogen atom, 84 and of the salts thereof, characterized in that it comprises the reaction of a) Masocyanate or isothiocyanate of general formula (IV) I in which is as defined above, with an aminopyrimidine or aminotriazine derivative of formula (III) (III) in which the substituents are as defined above at a temperature of from 0 to 50 ° C, preferably from 20 to 30 ° C, or (t)) a sulfonylcarbonate of general formula (V) Og-BH-OOR wherein it is as defined above, with an aminopyrimidine or aminotriazine derivative of formula (III) at a temperature of from 25 to 120 ° C, preferably at 60 to 90 ° C, or (c) a carbamoyl of general formula (VI) R 2 -CH-OR 3 in which the substituents are as defined above, with an alkali metal salt of a sulfonamide derivative of general formula (II) (II) in which the substituents are as defined above, at a temperature in the range of 10-50 DEG C., preferably 0 DEG-25 DEG C., or an E-pyrimidinyl carbamate or an N-trihinylcarbamate of the general formula VII) R 2 -CH-O-R 3 in which the substituents are as defined above, with a sulfonamide derivative of the general formula (II), in which the substituents are as defined above, at a temperature comprised between 20 and 80 ° C, preferably , between 20 and 40 ° C, or a sulfonyl chloride of general formula (VIII) R 1 in which the substituents are as defined above, (VIII) with an aminopyrimidine or aminotriazine derivative of the formula (III) wherein the substituents are as defined above, at a temperature in the range of 20 to 120 ° C, preferably at 60 to 90 ° C in an inert organic solvent or a mixing of organic solvents and then optionally converting the compound (I) thus obtained into a salt thereof by reaction with an alkali metal or alkaline earth metal hydroxide in an amine or a quaternary ammonium halide and separating the compound of formula (I) or its salt thus obtained by evaporating the solvent or solvents and, if necessary, by recrystallizing from the solvent. A process for the preparation of a herbicidal composition, preferably in the form of a wettable powder or granules, which is cooled by mixing with an active ingredient a substituted sulfonylurea derivative of the general formula (I) in which R1 is hydrogen, halogen, C1 -C4 haloalkoxyalkoxy, C1 -C4 alkylsulfonyl, or a group of the formula COR2 R2 denotes hydrogen, C1 -C4 alkyl or phenyl; means a C1 -C6 alkyl, a C1 -C6 alkenyl, a C1 -C4 alkoxyalkyl group, a C1 -C6 alkyl group substituted by one or more halogen atoms or benzyl, R4 and R5 independently of one another are C1 -C4 alkyl, C1 -C4 alkoxy, halogen, C1 -C6 alkylamino, di- (C1 -C6 alkyl), piperazinyl or morpholino, Σ means oxygen or sulfur and B means a methine group or an atom (I) as the active ingredient and an antidote, characterized in that the compound of the formula (I) is a compound of the formula (I) as an active ingredient and an antidote. (I) in which R 1, R 2, R 3, R 4, R 7 and R 10 are the same as defined in claim 1 or salt thereof as the active ingredient and an antidote, preferably I diacetyl-N-allylglycin-I'-allylamine (D-67), N, N-diallyl-dichloroacetamide (D-67), N-diisopropylethylamine R-25788), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG 191), 14β- (1,3-dioxolan-2-ylmethoxy) -imino-benzene-4-onenitrile (CGA-92194) or β- (dieloroacetyl) hexamethyleneimine (21-354) in a ratio of active ingredient to antidote preferably in the range of about 1: 1 to 1% by weight, with a suitable carrier and / or diluent. 4a. A method for controlling the presence of weeds in culture, characterized in that prior to emergence or after emergence a herbicidal composition according to the preceding claim is applied in the soil in an amount which is preferably between 0 , 01 and 2 kg of active ingredient per hectare of treated soil. lisboa, January 30, 1991 0 Agent ------ * Industrial América da Silva Carvalho Official Agent of the PropHodada induetrial R, Castilho, 201-3. E.-10Q0 LISBON Televisions. 651339-654613