DD202976A5 - HERBICIDAL AGENT - Google Patents

Abstract

The invention relates to herbicidal compositions containing as active ingredient certain new 1,4-dihydropyridine compounds. These agents are particularly suitable for controlling weeds in cotton and sunflower crops. According to the invention, for example, a herbicidally active compound is prepared by reacting an anilide, formaldehyde and an aminoethylene compound with each other. The reaction is conveniently carried out in an organic solvent and at a temperature between 15 and 100 degrees Celsius.

Description

The invention relates to a novel herbicidal composition containing as active ingredient certain 1,4-dihydropyridine compounds.

Characteristic of the known solutions:

Derivatives of Λ , 4-dihydro-3-N-phenylcarbamoyl-pyridine have already been described in the literature. Thus, in FR-PS 2 248 028, the compound of formula II is described as a medicament.

However, this compound is not effective for use as a herbicide in agriculture.

Object of the invention:

The object of the invention was to provide a new herbicidal composition.

- 2 Presentation of the essence of the invention:

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The invention relates to a herbicidal composition which contains as active ingredient at least one 1,4-dihydropyridine compound of the general formula I in which the substituents have the meanings given below, the following text, unless stated otherwise, having the property "lower" in the context of organic group means that this group contains at most 6 carbon atoms.

In general formula I, R and R are the same or different and each represents a hydrogen atom or a lower alkyl group,

R means ~ either

the radical -COOH or an agriculturally acceptable salt, this radical with an inorganic base such as sodium hydroxide solution or potassium hydroxide solution or with an organic base, for example a primary, secondary or tertiary amine, such as a mono-,

Can form di- or trialkanolamine,

5 5

the radical -COOR, in which Yr is a lower alkyl group, or the cyano radical;

X is an atom or a group selected from: halogen atoms,. ,

lower alkyl groups, lower alkoxy groups, lower alkenyl groups, lower alkenyl-oxy groups, lower haloalkyl groups,

Amino groups optionally substituted with one or more lower alkyl groups, which may be the same or different, or by the radical -CO-R,

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wherein R is a lower alkyl group, lower alkoxy group, lower alkylamino group or dialkylamino group in which each of the alkyl groups may be the same or different and contains 1 to 6 carbon atoms, nitro group and cyano group;

η is an integer from 0 to 5, where, when n> 1, the substituents X may be the same or different.

The invention also relates to agents containing the tautomeric forms of the compounds of general formula I.

The compounds present in the compositions according to the invention differ from those of the abovementioned FR-PS 2 248 028. They generally have excellent herbicidal activity.

Among the compounds which correspond to general formula I, those which are particularly suitable are:

2 3

R and R "are the same or different and each represents a" hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

R is an alkoxycarbonyl group containing 2 to 6 carbon atoms or the cyano group ,. X is an atom or a radical selected from the halogen atoms, the alkyl groups having 1 to 4 carbon atoms, the alkoxy groups having 1 to 4 carbon atoms,

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the haloalkyl groups having 1 to 4 carbon atoms and the cyano group,

η is an integer and may mean O, 1, 2, 3 or 4, it being understood that when η> 1, the substituents X may be the same or different.

Among these compounds, a preferred subgroup due to their excellent herbicidal activity consists of compounds of general formula III in the

χ '' is an alkyl group having 1 to 3 carbon atoms, preferably the methyl or ethyl group, X ^ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably the methyl or the ethyl group,

X is a hydrogen atom or a halogen atom, preferably a chlorine atom or an alkyl group having 1 to 3 carbon atoms, and

Υ represents an alkyl group having 1 to 4 carbon atoms.

Among these preferred compounds, especially the following compounds are emphasized:

1,4-dihydro-3-N (2,6-diethylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine,

1, 4-dihydr O-3-N (2,6-dimethylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine,

1,4-dihydro-3-N (2,6-diethylphenyl) carbamoyl-5-methoxycarbonyl-2,6-lutidine,

1,4-Dihydro-3-N (2,6-ethyl-6-methylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine,

1,4-Dihydro-3-N (3-chloro-2,6-dimethylphenyl) -carbamoyl-5-methoxycarbonyl-2,6-lutidine.

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These compounds are described as Compound Nos. 1, 3, 4, 14 and 20 in the following Examples.

The compounds of general formula 1 are prepared ^by: that the anilide der.allgemeinen formula IV, the formaldehyde of the general formula V and the Aminoäthylenverbindung of the general formula

2 "5 4

VI is reacted with one another, wherein X, n, R, Fr and R have the same meaning as in the general formula I. The reaction is carried out according to the following reaction scheme:

IV + V + VI> 1 + 2H ₂ O

The reaction is exothermic. It takes place in organic solvent already from room temperature. It can also be carried out at elevated temperature. - Of course, this temperature must be lower than the temperature at which the thermal decomposition of the starting compounds and entstaa products takes place. Temperatures between 15 and 100 ⁰ C generally lead to good results.

GeeigxEte solvents are the customary, protic or aprotic organic solvents, such as aromatic hydrocarbons, aliphatic or cycloaliphatic hydrocarbons, halogenated hydrocarbons, lower alkanols, such as methanol, ethanol, isopropanol, tert-butyl alcohol, ethers, such as diethyl ether, nitriles, such as acetonitrile, Amides, such as dimethylformamide. Advantageously, the reaction is carried out at the reflux temperature of the solvent used. If necessary, the reaction can be carried out in a closed container or under inert gas, for example nitrogen.

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The reaction takes place as soon as the three reactants of the general formulas IV, V and VI have been combined. For this purpose, it is advantageous to dissolve the anilide IV and the amino-ethylenic compound VI in a suitable solvent and then to allow the aldehyde V to act on the resulting solution.

The reaction product I is separated from the reaction mixture in a conventional manner; Generally, it crystallizes from this mixture by simply cooling. It can then be purified by recrystallization from a suitable solvent, liquid phase chromatography, etc.

The starting compounds corresponding to the general formulas V and VI are commercially available. The anilide of general formula IV can be prepared according to the method described in "Organic Syntheses", Vol. 3, page 10, starting from appropriately suitable starting compounds.

-Ausführungsbeispiele;

The following non-limiting examples illustrate the preparation of the compounds of the invention and their herbicidal properties. The structure of the compounds was confirmed by IR spectrum or by their KMR spectrum; the spectra were recorded at 60 MHz in DMSO (dimethylsulfoxide) with hexamethyldisiloxane as internal standard.

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example 1

Preparation of 1,4-dihydrc-3-N (2,6-diethylphenyl) -carbamoyl-5-ethoxycarbonyl-2,6-lutidine (Compound No. 1) of the formula

VII

In a 250 ml three-necked flask, equipped with condenser, thermometer and central mechansichem stirrer were submitted:

23.3 g (0.1 mol) of 2,6-diethylacetoacetanilide,

- 12.9 g (0.1 mol) of ethyl-.beta.-aminocrotonate and

- 50 ml of ethanol.

Wurde.gerührt the mixture "then heated from room temperature to 35 ° C until the reaction partners had completely dissolved and after cooling to 20 ⁰ C the mixture was added 10 ml of an aqueous 30 wt in the course of one minute, -.% - solution of formaldehyde (about 0.1 moles) was added. the reaction was exothermic and the temperature rose spontaneously from 20 ⁰ C to about 55 ° C to ". the reaction mixture was then heated for 60 minutes under reflux,

After cooling to room temperature, filtering off and väschen the precipitate with water to obtain

/8th

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14.5 g of a mixture of the desired compound and of 1,4-dihydro-3,5-di (ethoxycarbonyl) -2,6-lutidine, which had been formed by condensation of 2 moles of ethyl β-aminocrotonate with one mole of formaldehyde.

Recrystallization from 250 ml of ethanol gave 9 g of compound no. 1. Yield based on acetoacetanilide 25 %; Mp 209 ⁰ C; Molecular formula; C ^ H oN--O- ,.

The 2,6-diethyl acetoacetanilide used at the beginning was prepared by the action of 2,6-diethylaniline on diketene according to the method described in "Organic Syntheses", Vol. 3, page 10 for acetoanilide.

Example 2

Preparation of compounds Nos. 2 to. According to the procedure described in the preceding example, starting from the corresponding starting compounds, the compounds Nos. 2 to 23 were prepared. The formulas and physico-chemical properties of these compounds are listed in Table Ά below. __

Example 3

Preparation of Compound No. 24. According to the method described in Example 1, 1,4-dihydro-3-N (2,6-diethylphenyl) carbamoyl-5-cyano-2,6-lutidine was prepared from the corresponding compounds. Mp 200 ⁰ C ;. Empirical formula C ₁₉ H ₂₃ N ₅ O; From prey 84 %.

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B e is ρ ie 1 4

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Greenhouse herbicidal activity, pre-emergence test.

In 9 x 9 x 9 cm pots, filled with light field soil seeds were seeded, the number of which was based on the considered plant species and the thickness of the seed., Then the seeds were covered with an approximately 3 mm thick layer of soil.

After moistening the soil, the pots were sprayed with a slurry in an amount corresponding to a volume of 500 l / ha containing the active ingredient in the considered dose.

The slurry was prepared by diluting a wettable powder of the following composition with sufficient water to obtain the desired concentration:

- Test substance. 20 %

- inert solid carrier: kaolinite 69 %

surfactant - deflocculant: calcium lignosulphonate 5 %

surfactant wetting agent: sodium isopropylnaphthalenesulfonate ' Λ%

- silica as a means of Verhinde- -

lump formation 5 % *

This powder was obtained by mixing and finely grinding the components to a mean particle size below 40 / um.

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Depending on the active ingredient concentration in the slurry, the application rate of test substance was 2 to 8 kg / ha.

The treated pots were then placed in "jars" where they were watered from below and kept at below 70 % relative humidity for 35 days at room temperature.

After 35 days, the living plants were counted, which were treated in the Wi rks to ff-Aufschlmmung

'' .J pots were present, as well as the plants in control

Pots treated under the same conditions with a slurry without test substance In this way, the percentage of plants destroyed relative to the control experiment was determined. A quota of 100 % means that the considered plant species has been completely destroyed; A depreciation of 0 % means that the number of live plants in the treated pot is identical to the number of plants in the untreated control pot.

(The experiments. Were carried out with the following plants

leads:

weeds

Wild Oats (Avena fatua) Af

'Fingergrass (Digitaria sanguinalis) Ds

Barnyardgrass (Echinochloa crus-galli) Ec

Raygrass (Lolium multiflorum). Lm

Giant Fox Tail (Setaria faberii) Sf

Foxtail Grass (Alopecurus myosuroides) Am

Goosefoot (Chenopodium sp) Ch

black nightshade (Solanum nigrum) Sn

Ackersenf (Sinapis arvensis) Sa

Chickweed (Stellaria media) St

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crops

Cotton (Gossypium barbadense) Gb

Sunflower (HeIlanthus annuus) Ha

The results are summarized in the following Table 2. ,

These results show the excellent herbicidal activity of the compounds of the present invention over the majority of the treated weeds, both weeds and dicotyledonous weeds, and the selectivity to the contemplated crop plants.

For practical use, the compounds of the invention are rarely used alone, usually in the form of agents which are part of the invention and which generally contain, in addition to the active ingredient according to the invention, one or more liquid or solid carriers suitable for agricultural use / or one or more surfactants.

As the carrier in the present case, an organic or inorganic substance of natural or synthetic origin is referred to, with which the active ingredient is combined to facilitate the application to the plants or to the soil. The carrier can be solid - clays, natural or synthetic silicates, silicic acid, resins, waxes, fertilizers, solids and the like. a. m., or liquid ·.-.- water, alcohols, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases u. a. m.

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· - 12 -

23 180 6 3

The surface active agent may be an emulsifying agent, a dispersing agent, a deflocculating agent or a wetting agent, and also ionically 'or nonionic be _e Examples are salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic or naphthalenesulfonic acids, polycondensates of ethylene oxide and fatty alcohols or fatty acids or fatty amines, substituted Phenols, in particular alkylphenols or arylphenols, salts of sulfosuccinic acid esters, taurine derivatives ¹ , in particular alkyl taurate, phosphoric acid esters of alcohols or polyoxyäthylierten phenols.

Generally, compositions of the invention usually contain from 0.001 to about 95 wt -.% Of one or more compounds according to the invention. Their content of surfactant is generally 0 to 20% by weight .

The compositions may also contain various other ingredients such as thickeners, tuotropic agents, protective colloids, adhesives, penetrants, stabilizers, etc., as well as other known active ingredients having pesticidal properties, especially herbicides, fungicides and insecticides or having properties that promote plant growth, especially fertilizers , or with properties that control plant growth. In general, the compounds of the present invention can be combined with any solid or liquid additive commonly used in the manufacture of pesticides.

The compositions according to the invention can be used in the form of wettable powders, dusts, granules, solutions,

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emulsifiable concentrates, emulsions, .Suspensions- __konzentraten and aerosols are produced.

The wettable powders or powders typically contain 20 to 95 % by weight of active ingredient and generally contain, in addition to the solid support, 0 to 5 wt.% Wetting agents, 3 to 10 wt.% Stabilizer (s) and / or other additives such as Penetrants, adhesives or anticaking agents, dyes, etc.

They are produced by mixing the components in mixers and by grinding in mills or other suitable comminution equipment, for example air mills, to obtain the desired particle size »

As an example, the following composition of a wettable powder with 80 wt. 96 active ingredient is given:

, Active substance (compound no. 1) '' 80 %

«Sodium alkylnaphthalenesulfonate · 2 %

, Sodium lignosulfonate 2 %

, Silica as anti-caking agent 3 %

, Kaolinite. 13 96.

Another example of a wettable powder is:

, Active substance (compound no. 3). 50 %

, Sodium alkylnaphthalenesulfonate 2 %

, Methylcellulose low viscosity 2 % ·

, Diatomaceous earth. 46 %.

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A third example of a wettable powder is:

, Active substance (compound No. 14) 90 %

, Sodium dioctyl sulfosuccinate 0.2 %

, synthetic silica 9.8 %,

The granules intended to be applied to the soil are generally made to have dimensions of 0.1 to 2 mm; they can be made by agglomeration or impregnation. Generally, the granules contain 0.5 to 25% by weight of active ingredient and 0 to 10% by weight of additives such as stabilizers, slow release modifiers (release retarders), binders and solvents.

The emulsifiable concentrations suitable for spraying usually contain 10 to 50 % by weight per volume of active ingredient. In addition to the drug and solvent, they may further contain, if necessary, 2 to 20 % by weight per volume of additives such as surfactants, stabilizer penetrants, rust inhibitors, dyes, and adhesives.

The suspension concentrates, which are also applied by sputtering, are made to give a stable flowable product which does not settle out; they contain customarily 10 to "75 parts by weight 96 of active ingredient, 0.5 to 15 wt .-% of surface-active agent, from 0.1 to 10 wt -.% Ihixotrope agents, 0 to 10% of suitable additives, such as antifoaming agents, corrosion inhibitors, stabilizers,

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* can

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Penetrants and adhesives and as a carrier water or an organic liquid in which the active ingredient is substantially insoluble. Certain solid organic substances or mineral salts may be dissolved in the carrier to help prevent sedimentation or as antifreeze for the water.

The aqueous dispersions and emulsions obtained by diluting the above-mentioned agents, in particular the wettable powders and emulsifiable concentrates with water, are also within the scope of the invention. The emulsions obtained in this way can be water-in-oil emulsions or oil-in-water emulsions and have a thick consistency such as mayonnaise.

All of these aqueous dispersions and emulsions or slurries can be applied to the crop plants to be treated by any convenient means, principally sputtering in dosages generally from 500 to 1,000 slurry per hectare.

As indicated above, the invention also relates to a method of weed control in crop plants such as cotton and sunflowers wherein an effective amount of at least one of the compounds of the invention is applied to the plants and / or soil of the area in which weeds are to be disposed of becomes. In general, amounts of active substance of 0.5 to 10 kg / ha lead to good results, of course, the selection of the amounts of active ingredient to be used by the Inten-

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Depending on the climatic conditions and crops considered, the treatment is generally carried out prior to emergence of the crops and weeds or prior to sowing of the crops by soil treatment, in some cases depending on the conditions used compound good results are also achieved in post-emergence treatment.

Table A

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Table A

Compounds of formula Viii.

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Connection no. (X) rf \ / r5 Summation formula Fp ( ⁰ C) Out of booty 2  € ^ C ₂ H ₅ C ₁₈ H ₂₂ N ₂ O ₃ 164 29 3 CH ₃ ^U 3 i ^C 2 ^H 5 C ₁₉ H ₂₄ N ₂ O ₃ 159 20 4 ^C 2 ^H 5 C ₂₀ H ₂₆ N ₂ O ₃ 163 32 5 Cl C ₂ H ₅ : ₁₇ H ₁₉ C ^ ₂ O ₃ ICO .30 6 ¹ CH ₃ Z ₁₆ H ₁₇ CM ₂ O ₃ 125 67 7 Cl! C ₂ H ₅ Z ₁₇ H ₁₉ OH ₂ O ₃ 190 26 8th Cl Cl C ₂ H ₅ ^ 18 ⁰ W ₃ 136 30

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Table A (cont.) _

Verb in

fertil

No.

10

11 12 .13

it

CN

- <: ₂ h ₅

-C ₂ H

₂ H ₅

2 ^H 5 sunflower jacket

Fp ( ⁰ C)

yield

^: 17 ^H 2O ^N 2 ° 3

142

175

C ₁₉ H ₂₄ N ₂ O ₃

165

145

C ₁₈ H ₁₉ N ₃ O ₃

136

^C 2O ^H 26 ^N 2 ° 3

211

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Table A (cont.)

Connection no.

Molecular formula

F.O

( ⁰ C)

yield

15

16

CH

-C ₂ H ₅ -20 ^H 26 ^N 2 ° 3

165

CH

Rz ₂ H ₅ 140

33

26

17

OC ₂ H ₅ ^C 19 ^H 24 ^N 2 ° 4

117

'31

-CH 184

38

19

-C ₂ H ₅ 148

27

20

CI

-CH 175

2 0

21

22

C ₂ H ₅

^C 22 ^H 3 O ^N 2 °

180-185

-C ₂ H

₂ H ₅ C ₁₉ H ₂₄ N ₂ O ₃

166

89

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Table B

Herbicidal efficacy in the pre-emergence test 100

complete eradication no herbicidal action

Connection no. Dose kg / ha U. NKRÄUTER af ds ec Lm sf At the ch sn "sa st - crops Ha 1 2. 4 8 30 90 90 100 100 "100 80 100 100 80 80 100 100 100 100 100 100 100 100 100 ··, 100 100 100 100 15 50 95 100 100 100 gb 0.. 0 0 2 4 20 100 80 30 100 100 90 100 50 60 O O • 15 3 4 50 100 80 20 100 30 100 100 100 100 • 0 O 4 4 fi 60 60 100 100 100 100 ioo 100 80 90 90 100 100 100 100 100 95 100 100 100 0 "0 20 5 8th 40 - 40 30 - - 100 - 30 - 0 0 - 6 8th 90 100 O 80 '100 100 100 100 30 100 • 0 O

Table B (cont.)

Pre-emergence herbicidal activity 100 = complete eradication

= no herbicidal action

Verbin dose af WEEDS 'Ds ec LNT sf At the • ch sn • Sat St crops Ha No kg / ha 70 - 30 10 - - 100 l - 30 gb - 7 8th 20th 90 30 40 100  100 100 100 ¹ 20 100 - O 8th , 4 60 _ 30 20 I - _ 100 - 30 - O - 9 ' 8th 10 - 75 O - .80 ....... , .20 , .- - 10 8th 40 - · 100 90 - 100 - 100 - - , - 11 8th 20 - 30 30 - 100 - 50 - - , - 12 8th 10 - 75 20 - - 90 - O - - - 13 8th -

OO CD CD

Table B (cont.)

Pre-emergence herbicidal activity 100 = complete eradication

0 = no herbicidal action

Connection No. " Dose • kg / ha WEEDS af ds ec Lm Sf ^; At the ch sn Sat. St ' crops Ha ~ ^: 14 2 5 100 80 90 100 100 100 100 100 100 gb ' 0 15 8th 80 - 100 · 90 - - .10 ¹ O - 100 - 10 _ 16 8th 50.. -. PO 60 - 100 - 100 _ - - 17 8th 80 95 95 - - 100 - 20 - - - 18 8th 100 100 100 - - 100 - 100 - - - 19 8th 40 _ 95 90 - - 100 - 100 - - - 20 8th 100 - 100 100 - - 100 - 100 - - - 22 8th 30 '' 95 100 90 100 95 100 100 60 100th ! _w - 23 8th 100 95 - - 100 - 100 - ' - - -

23 180 6 3

formula sheet

H H

NH - CO

(X) n

(I)

H H

(ID

(III)

(j V _N H - CO - CH ₂ - CO - (IV)

H-CH-O (V)

q- C = CH - R

h (VI)

/ 2

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Formula sheet (cont.)

^C 2 ^H 5

H H

NH - CO

C ₂ H ₅

CO-O- C..H

^2H 5

CH ₃ V CH ₃

(VII)

(X) η

CO -

co - ο - r5

, (VIII)

CH, CH_H ^J

6224

ι η ο λ- * * 4 h Π 9 ί

, ο ρ, f

Claims (5)

invention claim 1. A herbicidal composition, characterized in that it contains, in addition to customary auxiliaries and excipients as the active ingredient at least one 1, ^ - Dih ^ dropyridin compound of general formula I, in the 2 3 - R and R- ^ are the same or different and each for a. H or an Alk ^ lgruppe having 1 to 6 carbon atoms; - R has one of the following meanings: the group -COOH or an agriculturally acceptable salt which may form this group with an inorganic base or with an organic base is the group COOir in which Tp is an alkyl group having from 1 to 6 carbon atoms, or the cyano group; - X stands for an atom, or a group of one of the following meanings j 231806 Halogen atoms, Alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkenyloxy groups having 2 to 6 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, amino group optionally substituted with one or more same or different alkyl groups each having 1 to 6 carbon atoms 1 1 or with the group -CO-R, wherein R is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms or a dialkylamino group in which each of the same or different alkyl groups Contains 1 to 6 carbon atoms,
Nitrοgruppe,
cyano group; - η is an integer from 0 to 5, where, when η.:> 1, the substituents X may be the same or different or a tautomeric form of these compounds. 2. Means according to item 1, marked in that the active ingredient is the general formula I owns, in the 2 3 - R and R are the same or different and a hydrogen atom or an alkyl group having 1 to 3 carbon atoms mean-4 R is an alkoxycarbonyl group containing 2 to Contains carbon atoms or represents the cyano group, - "- 23180 6 3 X is an atom or a group chosen from the halogen atoms, the alkyl groups having 1 to 4 carbon atoms, the alkoxy groups having 1 to 4 carbon atoms, the haloalkyl groups having 1 to 4 carbon atoms and the cyano group, - η is an integer and may mean O, 1, 2, 3 or 4, wherein when η> 1, the substituents X may be the same or different. 3. Means according to item 2, marked in that the active substance has the general formula III in which: X ^{1 is} an alkyl group having 1 to 3 carbon atoms, X ^{2 represents} a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, X is a hydrogen atom or a halogen atom or an alkyl group having from 1 to 3 carbon atoms, and , - Y represents an alkyl group having 1 to 4 carbon atoms. 4. Means according to point 3, marked in that the active substance is selected from the following compounds: 1,4-Dihydro-3-N (2,6-diethylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine, 1,4-dihydro-3-N (2,6-dimethylphenyl) -carbamoyl-5- ethoxycarbonyl-2,6-lutidine, 1,4-dihydro-3-N (2,6-diethylphenyl) carbamoyl-5-methoxycarbonyl-2,6-lutidine, 1,4-dihydr O-3-N (2,6-ethyl-6-methylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine, _: 1,4-Dihydro-3-N (3-chloro-2,6-dimethylphenyl) -carbamoyl-5-methoxycarbonyl-2,6-lutidine. 5. Composition according to item 1 to 4, characterized in that it contains 0.001 to 95 wt .-% of active ingredient. formulas 6223