DD200708A5 - HERBICIDAL AGENT - Google Patents

Abstract

The invention relates to herbicidal compositions containing as active ingredient certain new pyridine 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 and dehydrogenating the resulting 1,4-dihydropyridine compound to the desired pyridine compound. The first stage is conveniently carried out in an organic solvent at a temperature between 15 and 100 degrees.

Description

80

Title of the Invention: Herbicidal agent

Field of application of the invention:

The invention relates to a novel herbicidal composition containing Pyridih compounds as active ingredient.

Characteristic of the known solutions:

Derivatives of N-phenylcarbamoylpyridine have already been described in the literature. Thus, in European Patent Application No. OOO3IO5 the. Preparation of 2,6-dimethyl-3,5-dicarboxanilide-pyridine and stated that this type of compounds can be used as plant protection agents. 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:

The invention relates to a herbicidal composition containing as active ingredient at least one .Pyridin compound of general formula I, in which the substituents have the meanings given below, wherein in the following text, unless otherwise stated, the property "lower" in connection with Organic group means that this group contains at most 6 carbon atoms.

2 3

In general formula I, R and R 11 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 which this radical can form with an inorganic base such as caustic soda or potassium hydroxide solution or with an organic base, for example a primary, secondary or tertiary amine such as a mono-, di- or trialkanolamine, the remainder -COOR, in which R- denotes a lower alkyl group, or the cyano radical;

X stands for an atom or a group selected under:

Halogen atoms,. , ,

lower alkyl groups, lower alkoxy groups, lower alkenyl groups, lower alkenyloxy groups, lower enhaloalkyl groups,

Amino groups optionally substituted with one or more lower alkyl groups the same or

1 may be different, or by the remainder -CO-R,

/ 3

231 808 8

wherein R 'is a lower alkyl group, lower alkoxy group, lower alkyl on ino 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 compounds present in the agents according to the invention differ from those of the abovementioned European application. They generally have excellent herbicidal activity.

Among the compounds corresponding to the general formula I, especially those in which:

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 represents an alkoxycarbonyl group containing 2 to 6 carbon atoms or cyano, X represents an atom or a group selected from halogen atoms, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, and acyl groups having 3 to 5.Kohlenstoffatomen.

- ⁴ - 2318 08 8

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

η can be an integer "and C, 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 II in the

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

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

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

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

2,6-dimethyl-.3-N (2,6-dimethylphenyl) carbamoyl

5-ethoxycarbonyl-pyridine,

2,6-dimethyl-.3-N (2,6-diethyl-phenyl) -carbamoyl-1-ethoxycarbonyl-pyridine,

2., 6-Dimethyl-3-N (3-chloro-2,6-dimethylphenyl) carbamoyl-5-oxo-carbonyl-pyridine.

The connection ^! of general formula I can be prepared by a method that

/ 5

231 80

both successive stages A and B described below include:

Level A:

Preparation of 1,4-dihydropyridine of general

2 3 4 my formula III, where X, n, R, R, and R

have the same meaning as in formula I according to a method which consists in that one the anilide of the general formula IV, the formaldehyde of the general formula V and the

Aminoethylene compound of the general formula VI

2 3

in which X, n, R, R 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-: ^ III + H 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 takes place the thermal decomposition of the starting compounds and the entstai which products. Temperatures between 15 and 100 C generally lead to good results.

Suitable solvents are the customary, protic or aprotic organic solvents, such as aromatic hydrocarbons, aliphatic or cycloaliphatic hydrocarbons, and halogenated hydrocarbons.

231b ο

Hydrogens, 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.

The reaction according to step A 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 allow the aldehyde V to act on the resulting solution.

The reaction product III is separated from the reaction mixture in the usual way: generally, it is crystallized from this mixture by simple cooling or by addition of water.

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

Level B:

Dehydrogenation of the 1, 4-dihydropyridine of the general formula III to the pyridine compound of the general formula I.

ii

231808

This dehydrogenation can be carried out by means of processes known per se, which are described in particular in "Chemical Reviews", 1972, Vol. 72, No. 1, page 31, for example;

by the action of an oxidising agent, such as nitrous acid or nitric acid, generally produced in situ by the action of sodium nitrite on acetic acid, by chromic acid, iodine or sulfur,

by heating the dihydopyridine of general formula III, if necessary in the presence of a dehydrogenation catalyst such as palladium.

In the case of certain compounds prepared, it has also been observed that the dehydrogenation of the dihydropyridine to the corresponding pyridine sometimes occurs spontaneously, after a more or less long period, starting at room temperature without the use of catalyst.

Advantageously, the transition of the dihydropyridine of the general formula III to the pyridine of the general formula I is effected by the action of sodium nitrite on a suspension of the dihydropyridine of the general formula III in acetic acid. Since the reaction is exothermic, it is generally preferred that the reaction mixture be cooled so that its temperature does not exceed 25 ° C.

The pyridine of general formula I is separated from the reaction mixture by means of the usual procedures. Generally, the reaction product is precipitated by neutralization of the reaction mixture with an inorganic base such as ammonia. It can

/8th

231 80

then subsequently purified by conventional methods, for example by recrystallization from a suitable solvent such as ethanol, by liquid phase chromatography and others.

embodiments

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.

example 1

Preparation of 3-N (2,6-diethylphenyl) carbamoyl-5-ethoxycarbonyl-2,6-lutidine (compound no. 1), also as 2,6-dimethyl-.3-N (2,6-diethylphenyl) carbamoyl 5-ethoxycarbonyl-pyridine, of the formula VII _t

In a 250 ml three-necked flask fitted with a condenser, thermometer and central mechanical stirrer were charged:

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.

/ 9

The mixture was stirred and then warmed from room temperature to 35 ° C until the reactants had completely dissolved. After cooling to 20 ^° C., 10 ml of an aqueous 30% strength by weight formaldehyde solution (about 0.1 mol) were added to the mixture over one minute. The reaction was exothermic and the temperature rose spontaneously from 20 ⁰ C to about 55 C to _o The reaction mixture was then heated under reflux for 60 minutes.

Cool to room temperature, filter off and vase the precipitate with water

14.5 g of a mixture consisting of 1,4-dihydro-3-N (2,6-ethylphenyl) carbamoyl-5-ethoxycarbonyl -. -

2,6-I ^ I'din of the formula VIII

and by-product 1, 4-Dih.yd.ro-3, 5-di (ethoxycarbonyl) -2,6-lutidine, which by condensation of

2 moles of ethyl-β-aminocrotonate with one mole of formaldehyde

had arisen. \

After recrystallization from 250 ml of ethanol to give 9 g of 1,4-dihydro-N- (2,6-diethylphenyl) -3-carbamoyl-5-ethoxycarbonyl-2,6-lutidine, which melted at 209 ° C; Yield based on acetoacetanilide 25 % »

In the above described flasks were given:

- 5.5 g of 1,4-dihydro-3-N (2,6-diethylphenyl) -carbamoyl-S-ethoxycarbonyl, 6-lutidine obtained in the preceding Sufe and

- 55 ml of acetic acid. '

The reaction mixture was cooled to 16 ⁰ C and then treated in small portions with 1.2 g of sodium nitrite.

The exothermic reaction was controlled by cooling with an ice bath so that the temperature of the reaction mixture did not rise above 25 ° C.

2318 08 8

After stirring for 30 minutes at about 20 to 25 ^° C., the reaction mixture was poured onto ice and neutralized with 75 ml of concentrated ammonia. The resulting precipitate was filtered off and washed with water. After filtration over 120 g of silica and elution with a mixture of methylene and ether 8: 2 gave 4.2 g of the desired compound (compound no. 1).

- »Melting point 216 ⁰ C,

Yield, based on dihydrolutidine 77 %, - empirical formula ^ 21

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 30 According to the procedure described in the preceding example, compounds Nos. 2 to 30 were prepared starting from the corresponding starting compounds. The formulas and physicochemical properties of these compounds are listed in Table 1 below. The yields given in this table were calculated based on the acetoacetanilide used.

Example 3

Greenhouse herbicidal activity, pre-emergence test.

-23,180

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 grain _o Then the seeds were covered with about 3 now strong earth layer.

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

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 lignosulfonate 5%

surfactant wetting agent: sodium isopropylnaphthalenesulfonate 1 %

Silica as anti-lumping agent 5%

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

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

The treated pots were then placed in trays in which they were watered from below and were

2.3 1 8 08

Kept at room temperature below 70 % relative humidity for 35 days.

After 35 days, the live plants present in the drug-treated pots were counted and the plants in control pots treated under the same conditions with no test substance slurry. In this way, the percentage of killed plants, based on 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:

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 (Chenopodiura sp) Ch

black nightshade (Solanum nigrum) Sn

Ackersenf (Sinapis arvensis) Sa

Chickweed (Stellaria media) St

crops

Cotton (Gossypium barbadense) Gb

Sunflower (Helianthus annuus). Ha

2 318 0

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 use in practice, 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 of the invention, one or more liquid or solid carriers suitable for agricultural purposes 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 _e m., or liquid · .-: - water, alcohols, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquified gases Uo a · m.

The surface-active agent may be an emulsifying agent, a dispersing agent, a deflocculant or a wetting agent and ionic or non-ionic. Examples of these are salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensation

/ 14

2318 08 8

Products 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, in particular alkyl taurates, phosphoric acid esters of alcohols or polyoxyäthylierten phenols.

In general, the compositions according to the invention usually contain from 0.001 to about 95% by weight 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 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 prepared in the form of wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols.

The wettable powders or powders typically contain from 20% to 95% by weight of active ingredient and generally in addition to the solid carrier

/ 15

231808 8

O to 5 parts by weight of wetting agent, 3 to 10 parts by weight of stabilizer (s) and / or other additives such as penetrating agents, 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 .-% of active ingredient is given:

, Active ingredient (Compound No. 1) "80 % , sodium alkylnaphthalenesulfonate 2 %

_β sodium! sulfonate 2 %

, Silica as anti-caking agent 3 %

, Kaolinite '13 %.

Another example of a wettable powder is:

, Active substance (compound no. 1) 50 %

, Sodium alkylnaphthalenesulfonate 2 %

ο methyl cellulose good viscosity 2 %

, Diatomaceous earth 46 % *

A third example of a wettable powder is:

c drug (Compound No. 1) 90 %

, Sodium dioctyl sulfosuccinate 0.2 %

, synthetic silica S ₃ S%,

The granules destined to the ground

/ 16

-231808 8

being applied are generally made to have dimensions of 0.1 to 2 mm; they can be made by agglomeration or impregnation. In general, the granules contain 0.5 "to 25 wt .- # active ingredient and 0 to 10 wt .- # additives such as stabilizers, modifiers for the slow release of active ingredient (release retarder)., Binders and solvents.

The emulsifiable concentrates suitable for spraying typically contain 10 to 50 % by weight per volume of active ingredient. In addition to the active ingredient and the solvent, they may further contain, if necessary, 2 to 20 % by weight per volume of additives such as surfactants, stabilizers, 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 usually contain 10 to 75% by weight of active ingredient, 0.5 to 15% by weight of surfactants, 0.1 to 10% by weight of ibixotropic agents, 0 to 10% of suitable additives such as antifoaming agents, corrosion inhibitors, stabilizers, penetrating agents and adhesive 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. - * can

The aqueous dispersions and emulsions by

/ 17

- 2 3 I 8 O 8 8

Dilution of 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 may 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 crops to be treated by any convenient means, principally sputtering in dosages, which are generally from 500 to 1,000 slurry per hectare.

As indicated above, the invention also relates to a. A method for weed control in crops 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. In general, amounts of active ingredient of 0.5 to 10 kg / ha give good results, of course, the selection of the amounts of active ingredient to be used depends on the intensity of the problem to be solved, the climatic conditions and the contemplated crops. The treatment is generally carried out before emergence of the crops and weeds or before sowing the crops by soil treatment, and in some cases good results are obtained even after postemergence treatment after the compound has been used.

/ 18

TABLE 1

2318 08 8

Compounds of the formula IX

Connection no. .. O- ' Molecular formula Fp ( ⁰ C). From booty 2 ^ Cl ^C 17 ^H 18 ^N 2 ° 3 , 105 • 11 3 C ₁₇ H ₁₇ C ₂ O ₃ 136 4Ό 4 CH ₃ C ₁₇ H ₁₇ FN ₂ O ₃ 137 - Cr - 5 _{/ r} ^ ^C 2 ^H 5 C ₁₇ H ₁₇ ClN ₂ O ₃ 88 2 3 6 C ₁₇ H ₁₅ Cl ₃ N ₂ O ₃ 189 5.1 7 ^C 18 ^H 2 O ^N 2 ° 3 132 12 8th ^C 19 ^H 22 ^N 2 ° 3 188 ..4 9 ^C 2O ^H 24 ^N 2 ° 3 , 133 -

231808

• TABLE 1 (cont.)

- NH - CO

CH ₃

Connection

Molecular formula

fp

yield

IO

CH

^C 19 ^H 22 ^N 2 ° 3

187

17

11

^C 23 ^H 3 O ^N 2 ° 3

159

12

Q ₀ B ₁

3_ ^C 2O ^H 24 ^N 2 ° 3

203

19

13

^0CH

^C 18 ^H 2 O ^N 2 ° 4

86

14

CP

^C 18 ^H 17 ^F 3 ^N 2 ° 3

175

18.5

15

^C 18 ^H 16 ^C1 2 ^N 2 ° 3

174

16 162

15

/ 20

ZJIOUQ Q

TABLE 1 (cont.)

Compounds of the formula X.

Connection · No.

Buzzing formula

Fp ( ⁰ C)

yield

17

Cl

-COO-CH 16 ^H 15 ^CM 2 ° 3

Ί42

49

18

- CN ΛΑ

243.

⁶ 5

19

C ₂ H

-COXH ₃ 20 ^H 24 ^N 2 ° 3

192

25

20

-CCOC ₂ H

^C 19 ^H 22 ^N 2 ^D 3

185

12

21

CI

-COOC ₂ H

C ₁₉ H ₂₁ CM ₂ O ^

205

15

22nd

CH ₂ = C-CH

-CCOC ₂ H ₅ 20 ^H 22 ^N 2 ° 3

116

10

23

-rtc 95-96

24

^ CH

-COOCH = 19 ^H 22 ^N 2 ° 3

188

/ 21

(X) η

NH-CO-

CH.

CH.

Connection no.

(X) molecular formula

fp

( ⁰ o

yield

25

-COOC ₂ H ₅

^C 18 ^H 19 ™ 2 ° 3

156

26

Cl CH

-COOOL

207

27

BrCH

-CCOC ₂ H ₅

208

C ₀ H ₁

-CCOC ₂ H

₂ H ₅

C ₁₉ H ₂₂ N ₂ O ₃

188

Cl

-COOC ₂ H

₂ H ₅

^C 18 ^H 19 ^C1N 2 ^O 3

178

(CH ₃ )

-COOC ₂ H ₅

^C 21 ^H 26 ^N 2 ° 3

70

C ₁₇ H ₁₇ N ₃ O

243

/ 22

TABLE 2

Herbicidal efficacy pre-emergence test

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- · · 2 8th 10 90 50 5 100 20 100 100 30 O gb 0 3 8th 50 100 50 20 100 80 1ΟΌ 100 , .30 15 O - · 4 4 8 5. 20 80 100 30 50 10 20 100 100 20 40 80 100. 100 100. 10 50 Ul Ul - 0 5 8th ·' O 50 20 5 100 15 100 100. , 5th , 80 O O 6 8th O - O O - - 100 - 20 - O - 7 4 8 5 50 100 100 20 70 50 60, 100 100 80 .100 70. 95 100 100. 30. .40 20 40 - 0 8th 8th 50 - 90 .70. - - 100 - 80 - - - 9 8th .10 - 75 30 - - 100 - 60 - - - 10 2 4 8 5 50 80 100 100 100 " 50 50 80 10 50 50 100 100 100 20 20 70 100 100 100 100 100 100 25 95 95 95 100 100 '- 0 O 0 0 I

  TABLE 2 (cont.)

Herblzide pre-emergence efficacy 100 - complete eradication

= no herbicidal action

Connection no. Dose kg / ha WEEDS af 0 ds ec • Lm sf At the ch sn Sat. St crops Ha .H · 8th 0 - 0 0 - _ 80 _ 30 - gb - 12 4 0 100. 40  30th 30 100 60 100 ' , 60 100 - - 13 8th 0th - 20 20 - - 60,.   -_ 50 - - _. 14 8th 5 0 20; 40 0 60 0 90 I 100 0 50 - 0 15 I 8th 0 _ 80 50 · - - • 90 " 2 NC - - '0 - 16 8th , 90 20 20 0 95 20 90 100 0 100 ' - 0 17 • 8th 90 - .30 '80 - - • 30 - 60 - o. -. 18 8th 0, 60 - 30 '30 - 100 - 100 - _ - 0 0 19 1 4 100 ^: 100 60 95 80 95 100 100 90 100. 100 100 100 100 60 • RO 100 100 - V) 0'0 I

TABLE 2 (cont.)

Pre-emergence herbicidal activity 100 = complete eradication

··· · 0 t = no herbicidal action

/heiress- Dose kg / ha WEEDS af ds EC Lm sf At the ch sn Sat. st crops Ha, iung tfr. 8th 90 _ 100 60 - - - 100 - 100 - Gb " - 20 8th 95 - 100 100 - - 10Ό ~ "it 100 - - - • 21 8th 20 - 20 20 - - 100 - 20 - - - ²² . 8th · 20 - 30 20 - - lOO '   - 100 - - ' - 23  00 100 · 100 100   - - 100 l - 100 - - - 24 8th 90 - 100th 100 · - - 100 100 - - - 25 ", 8th "98 _ 100 100 - - 100 " 100 _ - - 26 8th 30 - , 98 , 80 - - 100 100 - -. - 27 8th ^{% <} 5 " 100 60 20 100 60 100 , 100th 20 100 - 0 28 8th . 0 98 90 10 100 3.0 100 100 80 95 0 0 29 8th 0 95 O , 0 , 95 20 100 100 0 100 0 0 30 8th 5 · 98 20 10 100   5th 100 100 20 0 • 0 0 31 0 t

See. ^ .. pages drawings

-dg- & m

formula sheet

NH - CO

(X) η

- NH-CO -υΤ <- COO, - Y

CH.

(II)

Η "H

NK - CO-

(X) η

(III)

7 \

NH - CO - CH ₂ - CO - R ^ (IV)

(X) η

H-CH-O

(V)

- C = CH -

"R '

(VI)

4L ^ ι w »-« '

Formula sheet (cont.)

NH - CO

^C 2 ^H 5

CO-O

_n H _c

⁴ CH, - CH-

(VII)

^C 2 ^H 5

H H

1311 - CO

^C 2 ^H 5

CO-OC ₀ H ₁ .

⁵ (VIII)

CH ₀

CH.

- NH - CO

CH

COOC ₂ H ₅

(IX)

(X) η

NH - CO-

CH

(X)

6227

- «η j, .Q h ~ '9FiR

Claims (5)

1. A herbicidal composition, characterized in that, in addition to customary auxiliaries and excipients, it contains as active ingredient at least one pyridine compound of the general formula 1 in which 2 3
R and R are the same or different and each represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; - R has one of the following meanings: the group -COOH or an agriculturally acceptable salt which can form this group with an inorganic base or with an organic base, the group -COOR in which B is an alkyl group having 1 to 6 carbon atoms,
the cyano group; ι · X is an atom or a group has one of the following meanings: Halogen atoms, Alkyl groups of 1 to 6 carbon atoms, alkoxy groups of 1 to 6 carbon atoms, alkenyl group of 2 to 6 carbon atoms, alkenyloxy group of 2 to 6 carbon atoms, -i O M Π Ii -4Ci 1 J. t \ 231808 8 Haloalkyl groups having 1 to 6 carbon atoms, amino, optionally substituted with one or more identical or different alkyl groups each of 1 to 6 carbon atoms, 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, each of which is the same or different alkyl groups contains 1 to 6 carbon atoms,
Nitrοgruppe,
cyano group; · - η is an integer from 0 to 5, where if η> 1 _; the substituents X may be the same or different. 2. Composition according to item 1, characterized in that the active substance has the general formula I in which: 2 3 - R and Rr are the same or different and jp / eils represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R is an alkoxycarbonyl group which contains 2 to 6 carbon atoms or represents the cyano group, 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 alkenyl groups having 3 to 5 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. - * ~ £ ν-? JU W W V 3. Composition according to item 2, characterized in that the active substance has the general formula II, in which: - X is an alkyl group having 1 to 3 carbon atoms, Jr is 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. Composition according to item 3, characterized in that the active ingredient is selected from the following compounds: 2,6-Dimethyl-3-N (2,6-dimethylphenyl) carbamoyl-5-ethoxycarbonylpyridine, 2,6-dimethyl-3-N (2,6-diethylphenyl) carbamoyl-5-ethoxycarbonylpyridine, 2, 6-dimethyl-3-N (3-chloro-2,6-dimethylphenyl) carbamoyl-5-ethoxycarbonyl-pyridine. 5. Composition according to items 1 to 4, gekennzeich net characterized in that it contains 0.001 to 95 wt - . % Active ingredient.