HU193881B - Herbicide composition with regulating activity for growth of plants containing triazine derivatives as active agents and process for producing the active agents - Google Patents

Abstract

Compounds of the formula: <IMAGE> wherein X is bromo, chloro or nitro Y and Z are lower alkyl, are useful as herbicides and as plant growth regulants.

Description

The present invention relates to novel triazine derivatives of formula (I). In the formula

X is a chlorine atom or a nitro group,

Y and Z are the same or different C 1-4 alkyl groups.

The compositions of the invention are particularly useful as herbicides and, in the case of soy and wheat, as growth regulators.

Compositions containing the structurally closest active compounds, azgz N- (6-amino-1,3,5-triazin-2-ylaminocarbonyl) -benzenesulfonate, are disclosed in U.S. Patent No. 4,231,784. However, these preparations are for use as herbicides only and do not show growth regulating activity.

The active compounds of the compositions of the invention may be prepared by reacting a compound of formula II with an equivalent amount of an amine of formula III.

The reaction can be accomplished by:. a mixture of isocyanate and amine is heated in an inert reaction medium such as toluene with stirring until the reactants are dissolved. After this, the product can be recovered by conventional solvent removal procedures and further purified by conventional techniques.

Example 1

Preparation of 2-Chloro-N - [(6- (N-methoxy-N-methyl) amino-4-methoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide

Into a flask equipped with a dichloromethane and nitrogen gas, with a stirrer and a thermometer, 1.85 g (0.01 mol) of 2-amino-4-methoxy-6- (N-methoxy-N-methyl) amino-1,3 were charged. 5-triazine and 2.2 g (0.01 mol) of 2-chlorobenzenesulfonyl isocyanate. The reaction mixture was stirred at room temperature overnight and dichloromethane was removed by distillation. Ethyl acetate (25 mL) was added to the residue and the solution was heated to reflux, then cooled to room temperature and filtered. 1.7 g of product are obtained, m.p. 181-183 ° C. Analysis results:

Calculated: C 38.76%, H 3.75%, N 20.86%; Found: C, 38.45; H, 3.73; N, 21.17.

Example 2

Preparation of 2-Nitro-N- [6- (N-methoxy-N-methyl) amino-4-methoxy-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide

Into a flask containing 100 ml of dichloromethane and nitrogen gas, with stirring and thermometer, was added 1.85 g (0.01 mol) of 2-amino-4-methoxy-6- (N-methoxy-N-methyl) amino-1, 3,5-triazine and 2.28 g (0.01 mol) of 2-nitrobenzenesulfonyl isocyanate. The reaction mixture was stirred at room temperature overnight.

If the TLC analysis shows that the reaction is incomplete, the reaction mixture is stirred for an additional 24 hours. If the chromatographic assay shows no change in the reaction, a small amount of isocyanate is added to the reaction mixture. after 5 days, the dichloromethane was removed by evaporation and boiling ethyl acetate (25 mL) was added to the residue; The mixture was cooled, filtered to give a white solid which was dried and analyzed by thin layer chromatography.

The desired product weighed 2.0 g, m.p. 178-180 ° C.

Analysis results:

Calculated: C 37.77, H 3.66, N 23.72; Found: C, 37.83; H, 3.76; N, 23.51.

The following compounds can be prepared as described in the examples above:

2-Bromo-N - [(6- (N-methoxy-N-methyl) -amino-4-methoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -benzenesulfonamide,

2-Nitro-N - [(6- (N-methoxy-N-isopropyl) -amino-4-ethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -benzenesulfonamide,

2-Chloro-N - [(6- (N-methoxy-N-ethyl) -amino-4-butoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -benzenesulfonamide,

2-Bromo-N - [(6- (N-methoxy-N-hexyl) -amino).

-4-Pentoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -benzenesulfonamide. ι

For practical use, the active compounds are formulated with herbicidal formulations using inert carriers. Such formulations allow the active ingredient to be applied in any suitable amount to the area infested with weeds. These formulations may be in the form of solids, such as powders, granules or wettable powders, or liquids such as solutions, aerosols or emulsifiable concentrates.

For example, powder formulations may be prepared by grinding and mixing the active ingredient with a solid, inert carrier such as talc, clay, silica, pyrophyllite or the like. For example, granular formulations may be prepared by impregnating a particulate carrier such as attapulgite or vermiculite having a particle size of generally 0.3 to 1.5 mm with a solution of the active ingredient in a suitable solvent. Wettable powders which are dispersible in any desired concentration of water or oil can be prepared by incorporating wetting agents in concentrated powder formulations.

In some cases, the active ingredient is sufficiently soluble in common organic solvents such as kerosene or xylene and may be used directly in the form of solutions in such solvents. Solutions of the active compounds can often be dispersed under high pressure and used as an aerosol. Preferred liquid herbicidal compositions, however, are emulsifiable concentrates consisting of an active ingredient and a solvent and emulsifier as an inert carrier. Such emulsifiable concentrates may be any water and / or oil

-2193881 can be diluted to the desired drug concentration and applied as a spray to the weeds. In such concentrates, nonionic surfactants or a mixture of nonionic and anionic surfactants are most commonly used as emulsifiers. Some emulsifier systems can produce an invert emulsion (water-in-oil) which can be used directly.

The composition of the herbicidal compositions of the invention is as follows; example.

Example 3

Preparation of Powder Formulation Composition: 10 parts by weight of the active ingredient, the product of Example 1 is by weight with powdered talc.

Example 4

Wettable Powder Composition: 81 parts by weight of active ingredient, product of Example 1,

14.8 parts by weight of kaolin, parts by weight of sodium lignin sulphonate,

0.2 parts by weight of sodium dioctylsulfosuccinate.

The ingredients are mixed in a mechanical grinding mixer and ground until a homogeneous free flowing powder of the desired particle size is obtained. This powder formulation can be applied directly to the weed infested area.

The herbicidal compositions of the invention may be applied in conventional manner. According to one herbicidal method, a composition comprising an inert carrier and an amount of herbicidal agent is applied to the weed area. The active compound concentrations of the herbicidal compositions according to the invention may vary within wide limits depending on the type of formulation and the intended purpose, generally between 0.5% and 95% by weight. A preferred embodiment of the composition according to the invention comprises 5 to 75% by weight of the active ingredient. The compositions may be admixed with other substances, such as other pesticides, such as insecticides, nematocides, fungicides, and may also contain stabilizers, dispersants, deactivators, adhesives, fertilizers and activators.

The compounds of the present invention are also active in herbicidal compositions in combination with other herbicides and / or disinfectants, growth inhibitors and the like. These other substances may constitute between 5% and 95% of the active ingredient in herbicidal compositions. When used in combination with other herbicides and / or herbicides, the herbicidal compositions of the present invention are more effective in controlling weeds and often exhibit effects which cannot be achieved by the use of each herbicide separately. Examples of other herbicides, decongestants, and plant growth inhibitors that can be effectively combined with the herbicides of the present invention for herbicidal purposes include: herbicides containing chlorophenoxy derivatives such as 2,4-D;

2,4,5-T, MCPA, MCPB, 4- (2,4-DB), 2,4-DEB, 4-CPB, 4-CPP, 2,4,5-TB, 2,4,5- TES, 3,4-DA, silvex; carbamate-containing herbicides such as IPC, CIPC, swep, barban, BCPC, CEPC CPPC; herbicides containing thiocarbamates and dithiocarbamates such as DCEC, EPTC, diaylate, PEBC, perbulate, vernolate; herbicides containing substituted ureas such as norea, siduron, dichloralurea, chloroxuron, cycluron, fenuron, monuron, monuron TCA, diuron, linuron, monolinuron, neburon, furniture, trimeturon; herbicides containing symmetric triazines such as simazine, chlorazine, desmethrin, norazine, ipazine, promethrin, atrazine, triethazine, simeton, promethone, propazine, amethrin; herbicides containing chloroacetamides such as α-chloro-Ν, Ν-dimethylacetamide, CDEA, CDAA, α-chloro-N-isopropylacetamide, 2-chloro-N-isopropylacetanilide, 4- (chloro- acetyl) morpholine, 1- (chloroacetyl) -1-piperidine; herbicides containing chlorinated aliphatic acids such as TCA, dalapone, 2,3-dichloropropionic acid, 2,2,3-TPA; chlorinated benzoic acids and phenyl- herbicides containing acetic acids such as 2,3,6-TBA, 2,3,5,6-TBA, dicamba, tricamba in which phenac, PBA, 2-methoxy-3,6-dichlorophenylacetic acid, 3- methoxy-2,6-dichlorophenylacetic acid, 2-methoxy-3,4,6-trichlorophenylacetic acid, 2,4-dichloro-3-nitrobenzoic acid, and active ingredients such as amino -triazole, maleic hydrazide, phenylmercuric acetate, endothelium, biuret, chlordane technical, dimethyl 2,3,5,6-tetrachloroterealate, diquat, erbon, DNC, DNBP, diclobinyl, DPA, diphenamid, dipropalin , trifluoraline, solan, dicryl, merphos, DMPA, DSMA, MSMA, potassium azide, acrolein, benefin, benzulide, AMS, bromacyl, 2- (3,4-dichlorophenyl) -4-methyl- 1,2,4-oxadiazolidine, 3,5-dione, bromoxynil, cacodylic acid, DMA, DPMF, cypromide, DCE, DCPA, dichlone, diphenatril, DMTT, DNAP, EBEP, EXD, HCA, ioxynil, IPX, isocryl, potassium- cyanate, MAA, MAHA, MCPES, MCPP, MH, molinate, NPA, OCH paraquat, PCP, picloram, DPA, PCA, pyrichlor, season, terbacil, terbutol, TCBA, brominyl, CP-50144, H-176-1, H -732, M-2091, planavin, sodium tetraborate, calcium cyanamide, DEF, ethyl xanthogen disulfide, syndone, syndone B, propanil.

These herbicides may be used in the form of their salts, esters, amides and other derivatives.

Weeds are unwanted plants that grow in places where they are undesirable, have no economic value and interfere with crop production, ornamentals or livestock development. The composition according to the invention can be used to control a number of weeds, including annuals, perennials such as hogweed, goat top, brush lawn, finger muff, wild rape, meadow grass.

-3193881 mulberry, french fescue, drought, chickpeas, wild oats, fluffy silvery, porcini, cockroach, peppermint, imola, sea buckthorn, tartare, broom, conceal, ragweed, chrysanthemum, senna, sorrel, curd, , dog milk, chickweed ,, millet, seaweed, dog dust, Mollungo verticillata, dawn, gall, duckweed and seaweed; biennial weeds, such as wild carrot, common grass, barley, thyme, chamomile, burdock, mite, broadleaf, thistle, tongue, moth and magenta; or perennials, such as white concubine, perennial wheat, common wheat, sorghum, wild aces, tufts, bermuda tree, wild mushroom, horsetail, marsupial, dandelion, bellflower, marsupial, russian cornflower, marshmallow, marshmallow, , scab, butterfly flower, sedge, meadow chops and winter cress.

Weeds can also be divided into broadleaf and grass groups. It is economically desirable to control the growth of weeds without damaging crop plants or livestock.

The compositions of the present invention are particularly useful for weed control because they are toxic to many weeds but relatively non-toxic to many crop plants. The amount of active ingredient required will depend on a number of factors such as the resistance of the weeds in question, the weather, the type of soil, the mode of application, the type of crop produced in the same area and the like. While satisfactory results can be obtained with 1-2 kg of active ingredient per hectare, if the weed infestation is mild and the weeds grow under unfavorable conditions, the equivalent of 10 kg per hectare or more may be needed if many resistant, perennial weeds grow under favorable conditions.

The herbicidal activity of the compositions of the invention is illustrated by the following pre-emergence and post-emergence experiments.

Pre-emergence studies were performed on a number of weeds. Small plastic pots were filled with dry soil and planted with seeds of many weeds. Up to 24 hours after sowing, the pots were sprayed with water to spray the soil and sprayed with water at the specified concentration on aqueous emulsions of test compounds prepared by mixing the desired amount of the active ingredient in 100 mL of 9 mL of acetone, 0.2 mL of dimethyl formamide, 0.8 ml methanol and 0.082% octylphenol polyethylene glycol ether in water.

After spraying, the pots were placed in a greenhouse where they received the required amount of heat and watered daily or more frequently. The plants were maintained under these conditions for 14 to 21 days, and the condition and degree of damage were evaluated on the following scale from 0 to 10:

no damage,

1, 2 slight damage

3, 4 moderate damage,

5, 6 moderate damage,

7, 8, 9 severe damage, destruction.

DO NOT mean that the plant has not hatched. The efficacy of the formulations containing each of the active compounds tested is given in the tables below.

EFFECTIVENESS OF PRE-BLOWER HERBICIDE TREATMENT days after treatment Active ingredient: Product of Example 1

kg / ha 1 0.5 0.25 0,125 charlock 9 10 9 9 convolvulus arvensis 8 8 8 9 pigweed 8 8 7 7 Selyemperj e 10 NOT 8 8 Morning glory 8 6 6 5 Fat Muhar 8 7 8 6 Barnyardgrass 9 9 8 5 johnson 7 5 2 0 Howitzer NOT 7 7 3 wild oats 5 2 2 0 Uj j asmuhar 8 6 5 2 Leptochloa 7 5 5 0 brome 8 7 8 6 Sugar beet 7 7 6 6 Soy-bean 9 9 9 9 Cotton 9 7 5 5 Pintobab 7 6 7 2 Alfalfa 5 7 5 5 Wheat 6 3 0 0 Rice 9 9 8 5 Sorghum 9 9 6 5 Maize 9 9 9 9 oat 4 4 2 0 datura 5 5 0 - BEFORE GOMING HERBICID TREATMENT effec-

WELLNESS days after treatment

Active substance: 1. 0.5 example 0.25 products 0,125 kg / ha charlock 9 10 9 9 convolvulus arvensis 8 8 8 9 pigweed 8 8 7 6 Selyemperj e 10 NOT 9 9 Morning glory 8 7 7 6

-4193881 kg / day after treatment Active ingredient: The product of Example 1 was 0.5 0.25

0,125

Fat Muhar

KakaslábfÖ

johnson

Howitzer

wild oats

crabgrass

Leptochloa

brome

Sugar beet

Soy-bean

Cotton

Pintobab

Alfalfa

Wheat

Rice

Sorghum

Maize

oat

datura

9 8 8 8 9 9

2 9 9

0

8 8 7

0 8 9

EFFECTIVENESS OF PRE-BLOWER HERBICIDE TREATMENT days after treatment Active ingredient: Product of Example 2

EFFECTIVENESS OF PRE-BLOWER HERBICIDE TREATMENT days after treatment Active ingredient: Product of Example 2 kg / ha 0.125 0.062 0.031 0.015

charlock

convolvulus arvensis

pigweed

silk Perje

Morning glory

Fat Muhar

KakaslábfÖ

johnson

Howitzer

wild oats

crabgrass

Leptochloa

brome

Sugar beet

Soy-bean

Cotton

Pintobab

Alfalfa

Wheat

Rice

Sorghum

Maize

oat

datura

8

5

8 9

5 5 2 9 8 9

NOT

1

NOT

3 7

1

5 5 4 4

NOT

0 7

4

NOT

2

0 0 2 1 7

NOT

kg / ha 8_ 4 2 0.5 0.25 Cyperus 5 2 1 0 charlock convolvulus arvensis 8 9 9 9 7 9 8 9 8 40 BEFORE GOMING HERBICID TREATMENT EFFECT- pigweed 7 8 8 8 9 7 STABILITY OF Selyemperj e Hajnalka Fat Muhar 8 7 8 7 7 9 7 7 9 8 8 9 NOT 8 9 NOT 8 7 21 days Active ingredient: after treatment: product of Example 2 KakaslábfÖ 9 9 9 9 9 9 45 kg / ha 8 , 4 2 0.5 0.25 johnson 8 9 8 7 8 7 charlock 7 10 10 10 9 9 Howitzer - - - 8 7 5 convolvulus arvensis - - - 8 8 7 wild oats 7 7 6 5 6 5 50 pigweed 6 9 9 7 7 7 crabgrass 7 9 9 9 8 8 Selyemperj e 7 8 8 8 NOT NOT Leptochloa - - - 8 9 7 Morning glory 5 7 7 8 8 8 brome NOT NOT NOT 9 9 9 Fat Muhar 7 9 9 9 9 9 Sugar beet - - - 8 8 7 KakaslábfÖ 9 10 10 9 9 9 Soybean - - 9 9 9 55 johnson 7 9 9 8 8 7 Cotton - - - 8 8 7 Howitzer - - - 9 8 7 Pintobab - - - 7 7 7 wild oats 5 8 7 7 6 7 Alfalfa - - - 4 5 5 crabgrass 6 9 9 9 9 9 Wheat - - - 8 6 5 Leptochloa - - - 9 10 8 Rice - - - NOT 9 NOT 60 brome NOT NOT NOT 9 9 9 Sorghum - - - 9 8 9 Sugar beet - - - 8 8 7 Maize - - - 9 9 9 Soybean - - - 9 9 9 oat - - - 7 5 4 Cotton - - - 8 8 8 datura 6 8 8 8 5 NOT 65 Pintobab - - - 7 7 7 Cyperus NOT NOT NOT NOT - - Alfalfa - - - 9 7 • 7

-5193881

21 days after treatment Active substance: : the 2. 1 ^ product of the living kg / ha 8 4 2 1 0.5 0.25 - · Wheat - - - 8 3 2 Rice - - - 8 9 NOT Sorghum - - - 10 9 9 Maize - - - 10 10 10 oat - - - 8 6 6 datura 7 9 9 9 8 NOT Cyperus NOT NOT NOT NOT - -

EFFECTIVENESS OF PRE-BLOWER HERBICIDE TREATMENT days after treatment Active ingredient: Product of Example 2

kg / ha 0,125 0.062 0.031 0,015 charlock 9 9 8 3 AprószuIák 7 NOT 3 3 pigweed 8 NOT NOT NOT Selyemperj e 5 4 2 1 Morning glory 7 6 5 3 Fat Muhar 8 6 3 1 barnyardgrass 8 7 5 4 johnson 6 NOT 4 2 Howitzer 7 4 3 0 wild oats 7 4 3 2 Uj j asmuhar 8 4 3 0 Leptochloa 5 - - - brome 9 10 6 6 Sugar beet 7 7 6 6 Soybean 9 7 5 4 Cotton 7 3 3 0 Pintobab 6 6 5 4 Alfalfa 7 7 4 4 Wheat 2 5 5 3 Rice 10 7 7 3 Sorghum 9 6 5 3 Maize 10 6 5 4 oat 6 6 5 10 datura 7 4 5 NOT Cyperus 6 2 0 0

The herbicidal efficacy of the compositions of the invention is also demonstrated by post-emergence studies on a number of weeds. The assays were performed by spraying the foliage of various weeds of a desired size with aqueous emulsions containing a fixed dose of each active ingredient. After spraying, the plants were placed in a greenhouse and watered daily or more frequently. The water was not applied to the foliage of the treated plants. The extent of damage was determined 14 days after treatment and as described in section 6 above

It was evaluated on a scale from 0 to 10. The efficacy is shown in the following tables.

EFFECTIVENESS OF AFTER TREATMENT HERBICID TREATMENT

Active ingredient: Product of Example 1

kg / ha 0, t j 0.25 0, 125 charlock 10 10 10 10 convolvulus arvensis 10 6 7 5 pigweed 9 6 7 10 Selyemperj e 10 10 9 7 Morning glory 8 8 9 6 Fat Muhar 8 8 7 8 barnyardgrass 10 10 9 8 johnson 5 5 0 0 Howitzer 10 10 2 0 wild oats 7 7 2 2 crabgrass 3 3 0 0 Leptochloa 5 2 0 0 brome 5 5 0 0 Sugar beet 10 10 10 10 Soy-bean 9 9 9 9 "Cotton 7 7 0 0 Pintobab 5 5 4 4 Alfalfa 10 9 7 10 Wheat 1 1 0 0 Rice 4 4 2 0 Sorghum 7 7 7 6 Maize 9 8 5 5 oat 6 6 2 0 datura 9 9 8 7 AFTER LEAVING HERBICIDE TREATMENT

EFFECTIVENESS

Active ingredient: Product of Example 2

kg / ha 4 2 1 * 0.5 * 0.25 * 0,125 ** · charlock Aprószu- 10 7 9 10 10 9 are contemplated Pig- 8 6 3 7 5 5 the grass on 8 8 9 9 7 7 Selyemper - 7 8 8 6 Hajnalka Fakó mu- 10 6 8 8 7 5 har Rooster- 10 10 9 8 7 7 foot grass 8 10 8 9 9 8 * 4 repetitions average * - * 3 repetitions average

-6193881

Active ingredient: Product of Example 2

2 1 * kg / ha

Grain sorghum Tarack Wild oat Fingers Leptochloa Rye Sugar beet Wool bean Cotton Spinach bean Lucerne Wheat Rice Sorghum Corn Oats

Maszlag 10 8 7

Cyperus 887

9 9

- - 9

4 7

4 6

- - 8

- - 7

- - 9

8 8

- - 7

- - 6

- - 8

- - 5

- - 6

- - 7

- - 8

- - 7

0.5 * 0.25 * 0.125 * »

7 6

7 6

5 4

4 2

6 2

7 6

10 10

8 9

5 1

5 1

9 8

4 2

6 6

6 4

8 6

6 5

In addition to its herbicidal activity, the compositions of the present invention also have a growth regulating effect on soybeans. Given the extensive nature of soy production, this is an important benefit. Growth control can be accomplished by contacting a preparation according to the invention consisting of an inert carrier and an appropriate amount of said active ingredient with a soybean acreage.

¹ θ The exact amount of active ingredient to be applied to soybean plants depends on many factors such as weather, soil type, method of application, presence of other plants in the area in question, etc. Generally, from about 0.001 to about 1 kg / ha, 15 tiers will provide the appropriate control effect, but in some cases less or more of the active ingredient will be required to achieve the desired result.

To determine the growth regulating properties of compounds shown in the above-described experiments were carried out before and after repeat sprouting soybean plants and Example 2 gave vei ²⁵ as test compound. Four different concentrations of active compound (0.125, 0.062, 0.031 and 0.015 kg / ha) were used, and the appropriate amount of the compound of Example 2 was mixed with the solvent mixture used for the herbicidal tests.

FOLLOW - UP TREATMENT

Active ingredient Biological 34 days 52 days kg / ha symptom after treatment experiment after treatment experiment

1. 2. 1. 2.

0.125 deaths 0 growth stops 9 development 7

0.062 deaths 0 growth stops 5 development 3

0.031 deaths 0 growth stops 3 development 2

0, .015 deaths 0 growth stops 0 development 1

0

9

0

0

5 2 2 0 0

0 0 4

The experiment showed a high degree of inhibition of apical meristem growth. Other phenomena shown by the test were: pronounced axillary rupture, distortion of the leaf bluish, and reduction in the size of the leaf bluish. At less than 0.125 kg / ha, most soybean shoots appear as branches growing from the axillary leaves of leafless leaves.

-7193881

PRE - TREATMENT

Active ingredient Biological 34 days 52 days kg / ha symptom after treatment after treatment

0.125 node growth growth stopping development

0.062 necrosis growth stopping development

0.031 necrosis growth stopping development

0.015 necrosis growth stopping development

In addition, the shape of the leaves has changed. Pre-emergence treatment experiment with soybean Active ingredient Biological kg / ha symptom experiment experiment

1. Second 1. Second 0 0 0 0 8 NOT 8 NOT 3 0 7 0 0 0 0 0 5 5 3 3 2 3 2 1 0 0 0 0 3 2 2 2 2 1 1 1 0 0 0 0 3 1 2 0 2 0 1 0 30 plant following using the product of Example 2, we repeated with the results: 14 day 21 day

post-treatment post-treatment necrosis growth stopping development yellowing

0.5 Necrosis Growth Stoppage Development Yellowing

0.25 necrosis growth stopping development yellowing

0.125 necrosis stopping growth yellowing

In addition, the soybean plants showed axillary fissure.

In another experiment on the growth-regulating properties of the composition of the invention, 8 aqueous emulsions of the product of Example 2 were mixed with the solvent mixture used in the previous experiments and the resulting compositions were added to the bottom layer of a 2-layer soil in an experimental bowl

-8193881, which allowed the root system to penetrate the lower soil layer. The experimental dishes were kept for six days in a dark place at 61 ° C. The results of the experiment were as follows.

In the evaluation, 0 means no effect and 10 means that neither root penetration into the lower layer nor shoot emergence from the upper layer is observed.

Active ingredient Soya kg / ha root shoot

1.0

0.2

0.04

0,008

0.0016

0.00032

0.000064

0.0000128

0

0

0

0

0

0

0

0

These two soil layer methods were also used in a further growth control experiment. In this experiment, the composition containing the product of Example 2 was applied to the lower layer and then to the upper layer.

Active ingredient mg / bowl or kg / ha

5.0 ', 0

0.2

0.04

0,008

0.0016

Soybean bottom layer root shoots top layer root root shoots

2.819 10 8 10 9 0.564 5 2 10 10 0.113 7 2 9 4 .0225 2 2 10 10 0.0045 5 1 10 9 0.0009 0 0 3 5

PATENT CLAIMS

Claims (5)

Claims 1. A herbicidal composition, characterized in that the inert carrier, preferably talc or kaolin, optionally a surfactant, preferably sodium lignin sulfonate or sodium dioctyl sulfosuccinate, and as active ingredient 0.0015-85% by weight (I). ) containing an N- (phenylsulfonyl) -N'5-triazinylurea derivative of the formula: X is a chlorine atom or a nitro group, Y and Z are the same or different C 1-4 alkyl groups. 10 The herbicidal composition according to claim 1, wherein the active ingredient is 2-nitro-N - [(6- (N-methoxy-N-methylamino) -4-methoxy-1, Contains 3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide. 3. The herbicidal composition according to claim 1, wherein the active ingredient is 2-chloro-N - [(6- (N-methoxy-N-methylamino) - Contains 4-methoxy-1,3,5-triazin-2-yl) aminocarbonyl] -benzenesulfonamide. 4. A growth regulator for plants, particularly soy, characterized in that the inert carrier, preferably talc or kaolin, optionally a surfactant, preferably sodium lignin sulphonate or sodium dioctylsulfosuccinate and 0.0015 to 85% by weight of active ingredient, contains an N- (phenylsulfonyl) -N'-triazinylurea derivative of formula (I) wherein 30 X chlorine or nitro, Y and Z are the same or different C 1-4 alkyl groups. 5. A process for the preparation of N-phenylsulfonyl) -N'-triazinylurea derivatives of the general formula (I) X is a chlorine atom or a nitro group, Y and Z are the same or different C 1 -C 4 alkyl groups, characterized in that the phenylsulfonyl isocyanate derivative of general formula (II) - in which X is as defined in the preceding paragraph - is 2,6-diamino- in general formula (III); with a 1,3,5-triazine derivative wherein Y and Z are as defined herein.