CS204033B2 - Herbicide means - Google Patents

Abstract

Compounds of formulae I and III which show activity as pre- and post- emergence herbicidal agents. <IMAGE> wherein X is hydrogen, alkyl C1-C3, halogen or nitro; R1 is alkyl C1-C4; R2 is alkyl C1-C6, cycloalkyl C3-C6, alkenyl C2-C4, phenyl, halophenyl or benzyl or when R1 and R2 are taken together with the carbon to which they are attached they may represent cycloalkyl C3-C6 optionally substituted with methyl; R3 is hydrogen, alkyl C1-C12 optionally substituted with one C1-C3 alkoxy group or one C3-C6 cycloalkyl group or one phenyl group or one furyl group or with one to three halogen substituent(s) preferably chlorine, alkenyl C3-C5 optionally substituted with one or two C1-C3 alkyl group(s) or one phenyl group with one to two halogen substituent(s) preferably chlorine, alkynyl C3-C5 optionally substituted with one or two C1-C3 alkyl group(s) or one phenyl group or with one to two halogen substituents preferably chlorine, benzyl, cyclohexenylmethyl, ethynylcyclohexyl, ethynylalkyl, pentadienyl or cycloalkyl C3-C6 optionally substituted with one or two C1-C3 alkyl group(s); or a salt formation cation of alkali metals, ammonium and aliphatic ammonium; and when R1 and R2 are not the same the optical isomers and the isomeric mixtures thereof; and except when R3 is a salt-forming cation, the acid addition salts thereof. - and - <IMAGE> wherein R1 is alkyl C1-C4; R2 is alkyl C1-C6, cycloalkyl C3-C6, alkenyl C2-C4, phenyl, halophenyl or benzyl; and when R1 and R2 are taken together with the carbon to which they are attached they may form cycloalkyl C3-C6 optionally substituted with methyl; R3 and R4 each individually represent hydrogen, alkyl C1-C4, alkenyl C3-C5, alkynyl C3-C5, or benzyl; and when R1 and R2 represent different substituents, the optical isomers thereof.

Description

The present invention relates to a novel herbicidal composition containing imidazolinylbenzoic acid derivatives as an active ingredient and to a process for the preparation of said active ingredient.

The subject of the invention is a herbicidal composition comprising, as an active ingredient, a compound of the formula I,

(I) in which is

X is hydrogen, alkyl of 1 to 3 carbon atoms, halogen or nitro,

R 1 is C 1 -C 4 alkyl,

R 2 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl

C 1 -C 4 alkenyl, phenyl or benzyl, wherein R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group which may optionally be substituted with a methyl group ,

R 5 is hydrogen, an alkyl group having 1 to 12 carbon atoms which may be optionally substituted by one alkoxy group having 1 to 3 carbon atoms or one cycloalkyl group having 3 to 6 carbon atoms or one phenyl group or one furyl group having 3 to 5 carbon atoms , which may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogen substituents, an alkynyl group having 3 to 5 carbon atoms which may be optionally substituted by one or two alkyl groups having 1 and 2 to 3 carbon atoms or one phenyl or one or two halogen substituents, benzyl, cyclohexenylmethyl, ethinylcyclohexyl, ethnynylallyl or pentadienyl, cycloalkyl having 3 to 6 carbon atoms, which may optionally be substituted with one or two alkyl groups having 1 to 3 carbon atoms, or a salt forming a cation consisting of an alkali metal, an ammonium group or an aliphatic ammonium group having a total carbon number of 1 to 18, or optical isomers thereof, and mixtures of these optical isomers, that Ri and R? have different meanings, or acid addition salts thereof, when R 3 is not a cation forming salt.

The herbicidal composition according to the invention preferably contains as active ingredient a compound of the formula I in which it is

X is hydrogen, methyl, chloro or nitro,

R 1 is an alkyl group having 1 to 3 carbon atoms,

R 2 is C 1 -C 3 alkyl or cyclohexyl, wherein R 1 and R 2 together with the carbon atom to which they are attached may form a cyclohexyl group or a methylcyclohexyl group,

R 3 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl which may optionally be substituted by one or two chlorine substituents or one or two C 1 -C 3 alkyl groups, C 3 -C 5 alkynyl group carbon atoms which may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms, a benzyl group, a cyclohexenylmethyl group or a pentadienyl group, as well as its optically active isomers and isomer mixtures when R 1 and R 2 have different meanings, and acid addition salts thereof when R 3 is not a cation forming salt.

It is particularly preferred that the herbicidal composition according to the invention contains as active ingredient a compound of the formula I in which it is

X is hydrogen, methyl or chlorine,

R 1 is methyl,

R2 isopropyl and

R 3 is hydrogen, an alkyl group having 1 to 12 carbon atoms which may be optionally substituted by one alkoxy group having 1 to 3 carbon atoms or one cycloalkyl group having 3 to 6 carbon atoms or one phenyl group or one furyl group, an alkenyl group having 3 to 6 carbon atoms 5 carbon atoms which may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogen substituents, an alkynyl group having 3 to 5 carbon atoms which may optionally be substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogen substituents, benzyl, cyclohexenylmethyl, ethinylcyclohexyl, ethinylallyl or pentadienyl, cycloalkyl having 3 to 6 carbon atoms which may e optionally be substituted by one or two alkyl groups having 1 to 3 carbon atoms or a salt forming cation, consisting of, alkali metal, ammonium or aliphatic ammonium group having a total carbon number of 1 to 18

Very preferably, the herbicidal composition according to the invention contains as active ingredient:

2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, 2-propioneleeter, methyl-4-isopropyl-5-methyl-4-oxo-4-imidazolin-2-yl) 2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid, isomeric 6- (5-isopropyl-5-methyl-4-oxo-2-methyl ester) -imidazolin-2-yl) -m-toluic acid and methyl 2- (5-isopropyl-5-methyl-4-oxo-2-imidazol-2-yl) -p-toluic acid ethyl ester (+) - 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolio-2-yl) benzoic acid; and

(+) -2- (5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid C-pentallyl ester.

The present invention also relates to a process for the preparation of an active compound of the formula I in which X, R 1, R a and R 3 are as defined above, as well as optical isomers and mixtures thereof when R 1 and R 2 have different meanings; acid addition salts when R @ 3 is not a cation forming salt, which comprises reacting a compound of the formula II;

wherein X, R 1 and R 2 are as defined above, with an alcohol of formula

R 5 -OH, wherein R 3 is as defined above, in the presence of an alkali metal or alkali metal hydride. at 20 to 50 ° C, whereupon the compound of formula I wherein R 3 is hydrogen is optionally converted to an acid addition salt.

In the process according to the invention, the ratio of alcohol to alcohol is. The compound of formula II is preferably in the range 1.1: 1 to 5: 1 and the reaction is carried out under an inert gas atmosphere.

Preferably, an aprotic solvent is added to the reaction mixture of the compound of formula II, an alcohol and an alkali metal or alkali metal hydride in an amount such that the ratio of the aprotic solvent to the alcohol does not exceed 4: 1 and the reaction. is carried out under an inert gas atmosphere.

In the process according to the invention, the alkali metal or alkali metal hydride is first mixed with the corresponding alcohol and the mixture thus obtained is mixed with the imidazoisoindole dione II.

Nitrogen, argon and helium may be used as inert gas to create an inert atmosphere above the reaction mixture, and preferably nitrogen may be used.

Sodium, sodium hydride, potassium, potassium hydride, lithium and lithium hydride may be used as the alkali metal and alkali metal hydride.

The process of the invention may be illustrated by the following reaction scheme:

wherein X, R 1, R 2 and R 3 are as defined above.

In these reactions, alcohol plays the role of both reactants and solvents. In this case, it is not necessary to use a secondary solvent. However, if it is necessary to use a relatively expensive alcohol in the reaction or if an excess of alcohol is necessary to produce optimal reaction conditions, it may be advantageous to add a less expensive secondary solvent such as dioxane, tetrahydrofuran or other aprotic solvent to the reaction mixture.

In the present case, the amount of the aprotic solvent to the reaction mixture may vary within wide limits; usually. this amount does not exceed four times the amount of reaction alcohol used. Thus, the ratio of secondary solvent to alcohol in the process of the invention may range from 0: 1 to 4: 1.

Compounds of formula I in which R3 is hydrogen may also be prepared by reacting an imidazoisoindole dione of formula II in which X, R1 and Ra are as defined above with an excess of hydrochloric acid in the presence of a water miscible solvent such as tetrahydrofuran or dioxane . The reaction results in the lactone hydrochloride of formula IV,

wherein X, R 1 and R 2 are as defined above, which is then reacted with one equivalent of a base, such as. sodium hydroxide, potassium hydroxide or sodium carbonate to give the corresponding acid. This reaction can be illustrated by the following reaction scheme:

wherein X, R 1 and R 2 are as defined above.

The above imidazolinylbenzoic acid can then be converted to the corresponding salt with an alkali metal, ammonium or aliphatic ammonium cation.

If it is desired to produce an alkali metal salt, the acid of formula I (R 5 = H) is treated with an aqueous alkali metal hydroxide solution and then the reaction water is removed, preferably by azeotropic distillation with an organic solvent such as dioxane.

The ammonium and aliphatic ammonium salts are prepared in a similar manner except that the acid of formula I is partially dissolved in a lower alcohol such as methanol, ethanol or isopropanol, and ammonia or the corresponding aliphatic amine is added to the solution. The reaction mixture is then concentrated and the residue thus obtained is treated with hexane and the mixture is then dried to obtain the ammonium or aliphatic salt of the acid of formula I.

The compounds of formula (I) above may be mixtures of the two positional isomers when X is other than hydrogen, since the imidazoisoindole dione intermediates of formula (II) are also mixtures of isomers when X is not hydrogen.

As can be seen from the following reaction scheme, compounds of formula II can be prepared from the corresponding phthalimidocarboxamide precursor by cyclization, where, when the general substituent X is different from hydrogen, cyclization occurs on both imidocarbonyl groups to form a mixture of the two resulting isomers:

wherein R1, R2 and X are as defined above, except that X is not hydrogen.

The imidazolinyl benzoates of formula (I) above may be tautomeric. For simplicity, these compounds, although included under the single structural formula I above, may exist in one of the following isomeric forms:

wherein X, R 1, R 2 and R 5 are as defined above. Due to the existence of the isomeric forms of the imidazolinyl benzoate compounds, both forms are within the scope of formula (I) above.

These compounds are also amphoteric. They dissolve in both acidic and basic aqueous solutions and, when treated with strong acids, especially strong mineral acids such as hydrochloric, sulfuric and hydrobromic acids, then form acid addition salts of the imidazolinyl benzoates of formula I.

It will also be appreciated that when R 1 and R 2 are different groups in the imidazolinyl benzoates of formula (I), the carbon atom to which R 1 and R 2 are attached is an asymmetric carbon atom. Therefore, said products (as well as intermediates leading to their preparation) exist in d-form, 1-form and dl-form.

The corresponding d- or 1-form is readily prepared by reacting the corresponding optically active d- or 1-imidazoisoindole dione of formula II with the corresponding alcohol of formula III to give the corresponding d- or 1-imidazolinylbenzoate of formula I.

The imidazoisoindole diones of the general formula II which are used as intermediates in the preparation of the imidazolinyl tertiates of the general formula I according to the invention are described in U.S. Pat. No. 4,017,510.

The compounds of the present invention are highly effective herbicides useful for controlling monocotyledons, cyperacaes and dicotyledons. Said compounds may be used for postemergence control of undesirable plant species by applying a herbicidally effective amount to the foliage of undesirable plants or for preemergence control of undesirable plants by applying a herbicidally effective amount of a herbicidally active compound of the invention to soil containing seeds, seedlings or fruiting bodies of undesirable plants.

Since the imidazolinyl benzoates of the formula I according to the invention have only limited solubility in water, they are generally applied as wettable powders, emulsifiable concentrates or liquids, which are usually dispersed in water or other cheap diluents suitable for spray application. The compounds of the invention may also be formulated as granules, containing generally about 10-15% herbicidally active agents.

A conventional wettable powder can be prepared by grinding up to 80% by weight together. % imidazolinyl benzoate, up to 5 wt. % surfactant, such as sodium N-methyl-Noleyltaurate, alkylphenoxypolyoxyethylenethanol or sodium alkylnaphthalenesulfonate, up to 10 wt. % dispersing agent, such as very pure sodium lignosulfonate, up to 63 wt. % finely divided carrier such as kaolin, attapulgite, diatomaceous earth and the like.

A typical formulation of this type comprises:

wt. % By weight of 2-propynyl-o- (5-isopeosyl-5-methyl-4-oxo-2-imidazolin-2-yl] benzoate,% by weight of sodium Nimethyl-NiOlpyltaurate,% by weight of sodium lignosulfonate and% by weight of kaolin.

The liquid formulation can be prepared by co-grinding up to 60% by weight. % of the amidazolyl benzoate of formula (I), i.e. 0 wt. % sonnt of the naphthalenesulfonic acid solnnnn 0% % 0 hiikky, mas,% pessylečglykslu and 54. up to 32 wt. % water.

Conventional granules may be prepared by dissolving or dispersing the active compound of the invention in a solvent and applying the treated compound to a sorbent or non-absorbent carrier such as attapulgite, corn cobs, pumice stone or talc.

As mentioned above, the imoisocyanate compounds of formula 1 are potent pre-emergence herbicides. These compounds are highly effective in controlling six-leafed and grass weeds when applied in an amount of about 0.07 to 11.2 kg. per hectare of soil, containing seeds, seedlings or organs of shingle-leafed, broad-leaved or grass-like plants.

The compounds of the present invention are also potent psstmergent herbicides of broadleaf, broadleaf and grass weeds when applied at a rate of 0.28-11.2 kg per hectare to the foliage of undesirable plants.

In addition to being herbicidally effective in controlling a variety of undesirable plant species, the compounds of this invention are the only herbicides that have the ability to efficiently control certain pale plants (Cyperaceae) at relatively low rates of application. of formula (I) are most effective for controlling pinged plants in pre-emergence application at application rates of 0.14 to 11.2 kg per hectare, of course, higher application rates may also be used if the plots under control are extremely intense. Under these conditions, the benzoates of the formula I can be applied postorally or at a rate of application of 25 kg per hectare.

Examples of the pice plants that can be controlled by the imidazolinyl benzoates of the invention are Cyperus rotunOus L., Cyperus esulentus L., Cyperus strigosus, Cyperus alternifolius.

In the following, the invention will be explained in more detail by way of examples.

Example. 1

Preparation of 2-Prosisnyl S- (5-isopropyl-5-methyl-4-oxo-12-imidanolic 2-cl} bennoate

0.1 g of a 50% suspension of sodium hydride in mineral oil was added to 12.5 ml of p -pargylalkyl. The addition of propyl carboxylic acid to the slurry is carried out under stirring under an atmosphere of nitrogen while maintaining the temperature of the resulting mixture in the range of 20 ° C to 25 ° C by external cooling. The formation of pespargylalkyl sodium is complete within one to two hours.

To this solution was then added 5 g of 3-isopropyl-3-methyl-5H-imidazo [2,1-a] isoisyl (3H), 5,150, and the reciting mixture was stirred at ambient temperature overnight under a nitrogen atmosphere. The reaction was incomplete and the reaction mixture was treated with an additional 50 mg of a 50% suspension of sodium hydroxide in oil.

After stirring the reaction mixture overnight, the mixture was cooled to 5 ° C and 0.7 ml of 3 N hydrochloric acid was added.

The reaction mixture was then diluted with methylene chloride

The organic phase is dried and concentrated in vacuo.

The crystalline residue is then transferred to a filter as a suspension in hexane and air dried to give 6.02 g of 2-propynyl-o (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate.

Melting point 131-144 ° C.

The product of a similar reaction was recrystallized from acetone-hexane to give pure product, melting at 145-147 ° C.

Example 2

The following imidazolinyl benzoates were prepared by essentially the same procedure described in the preceding Example 1, except that the propargyl alcohol was replaced with the corresponding alcohol and 3-isopropyl-3-methyl-5H-imidazo [2,1-a] isoindole-2 (3H). The 5-dione is replaced by the corresponding imidazoisoindole dlonone. This reaction can be illustrated by the following reaction scheme:

Preparation of the imidazolinyl benzoates of formula (I)

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• СНз — СН (СНз) 2 — СНг — СНг— Η 166—169

СНз — СН (СНз) з — СН (СНз) СН = СН — СНз 3 (6) С1 161—163

СНз —СН (СНз) 2 —С2Н5 3 (6) 1562,156—157

СНз —С2Н5 —СНз Н 135—136

СНз —С2Н5 —СНг — С = СН Н 137—139

R1 R2 R3 X Melting point (° C)

СНз - C2H5 —CH2 — С = СНг H 125—126

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R1 R2 R3 X Melting point (° C)

СНз —СН (СНз) 2 —CH2 — C = CH4 (5) C1 177—187

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Example 3

Preparation of 1,1-dmethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate hydrochloride

COOC (CH ₂ ) _Z CH = CH.

H CH _Z CH (CHJ,

COOC _(CH3) ZCH-CH _of ^CH 3 · HCl ^CHK Vz

To a solution containing 164 mg of 1,1-dimethylallyl-o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoate (0.5 mmol) in 5 ml of methylene chloride and 5 ml of absolute ethanol 0.5 ml of 1 N hydrochloric acid is added. The reaction mixture was concentrated in vacuo and ether was added to the residue to precipitate a crystalline product which was isolated by filtration, washed with ether and air dried to give 170 mg of the above hydrochloride. Melting point: 259 DEG-262 DEG C. [with decomposition].

The melting point of this and other salts is dependent on the heating rate.

Example 4

Preparation of o- (5-isopropyl-5-methyl-4-oxo-2-midazolin-2-yl) benzoic acid

To a stirred solution containing 5 g

3-Isopropyl-3-methyl-5H-imidazo [2,1-a] isoindole-2 (3H), 5-dione in 15 ml dioxane was added a mixture of 10 ml concentrated hydrochloric acid and 10 ml water. The reaction mixture is then heated to boiling and allowed to cool to ambient temperature.

The separated crystals were collected by filtration, washed with water and acetone and air dried. The filtrate was concentrated in vacuo and the precipitated and collected solids were washed with acetone and air dried. A total of 4.5 g of lactone hydrochloride having the above structure A is obtained in two portions. The melting point of this product is 265 DEG C. (with decomposition).

. To a stirred partial solution of hydrochloride (4.5 g) in 30 ml of water was added a solution containing 0.6 g of sodium hydroxide in 10 ml of water. The remaining solid dissolved within a few minutes and after a further fifteen minutes a solid precipitated out of solution, which was removed by filtration.

The filtrate was concentrated in vacuo, the solid collected by filtration and combined with the first solid, then the combined solid was washed with water and air dried to give 3.8 g of o- (5-isopropyl-5-methyl-4-). oxo-2-midazolin-2-yl) benzoic acid.

Melting point: 162-163 ^° C. An analytically pure sample of the same product had a melting point of 163-165 ° C.

Example 5

Salts of o- (5-isopropyl-5-methyl-4-oxo-2-midazolin-2-yl) benzoic acid

The sodium salt is prepared by adding 9.9 ml of 1 N sodium hydroxide solution with stirring to a partial solution of 2.58 g of imidazolinylbenzoic acid in 10 ml of water. After 1.5 hours the solution was concentrated in vacuo and the remaining water was then removed azeotropically with dioxane to give the hygroscopic sodium salt, melting at 184-188 ° C.

The amine salts are simply prepared in methanol. To a stirred partial solution of 5 g of imidazolinylbenzoic acid in 15 ml of methanol was added 3.17 ml of triethylamine. After 0.75 hours a clear solution was obtained. The solution was then concentrated and the remaining slurry was diluted with hexane and filtered; the solid was filtered off and dried to give the trisulfonyl salt. Mp 54-55 ° C.

The isopropylamine salt prepared in a similar manner has a melting point of 92-98 ° C.

Example 6

Preparation of o- (5-isopropyl-5-methyl-4-oxo-2-midazolin-2-yl) -N, N-dimethylbenzamide

To a cold solution of 180 g of 3-isopropyl204033

3-Methyl-5H-imidazole [2,1-a] isoindole-2 (3H), 5-dione in 300 mL of anhydrous tetrahydrofuran in a pressure vessel was added 68 g of dimethylamine. The pressure vessel was then sealed and the mixture was heated to 50 ° C with stirring for 16 hours.

The reaction mixture was cooled and transferred to a flask. The solvent was removed by vacuum distillation. The crystalline residue is then suspended in ether, the suspension is filtered, the solid is washed with ether and air-dried to give 195 g of o- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) -1, The product obtained melts at 144-146 ° C.

The product is then recrystallized from acetonitrile to give an analytically pure product, melting at 147-150 ° C.

Example 7

Preparation of imidazolinylbenzamides of formula III

Using essentially the same procedure described in Example 6, using the appropriate imldazo [2,1-a] isolndole-2 (3H), 5-dione and replacing the corresponding amine with dimethylamine yields the compounds listed in Table 2 below. .

Rž

Melting point (° C)

Ri

- (CH 2) 5— н н 211—212 СНз СН (СНз) 2 н н 174—175 СНз СН (СНз) 2 н СНз 203—204 - (СН2) 5— СНз СНз 189—190,5 - (СН2) 5- Ή СНз 259—261 СНз СН (СНз) 2 No. —СНгС ^ СН 202—205

Example 8

Post-emergence herbicidal activity

The post-emergence herbicidal activity of the compounds prepared by the process of the invention is determined by the following tests in which monocotyledons and dicotyledons are treated with dispersions of the compounds in water / acetone mixtures.

In these tests, the individual plants were grown separately for two weeks in pots. Test compounds are dispersed in acetone / water (50:50) containing 0.5% Tween 20 (a polyoxyethylene sorbitan monolaurate surfactant from Atlas Chemical Industries) in an amount such that an application rate of 0.07 to 11.2 kg is achieved. / hectare when applying said dispersion to the plant by means of a spray nozzle operated at a pressure of 280 kPa for a specified period of time.

After application of the active ingredient to the plant, the plants are placed in a greenhouse for treatment in the usual manner.

Two weeks after application (except species

Avena fatua), the condition of each plant is evaluated according to the following scale of plant damage. The status of Avena fatua is evaluated up to 5 weeks after the effective dose.

The results obtained are summarized in Tables 3 and 4 below.

Classification system

Growth differential with respect to the test where no active substance is applied (%)

0 - no effect 0 1 - possible effect 1—10 2 - weak effect 11-25 3 - medium effect 26—40 4 - final damage 41—60 6 - herbicidal effect 61—75 7 - good herbicidal effect 76—90 8 - almost complete death 91—99 9 - complete death 100 ALIGN!

Acronym Plant - abnormal growth and definitive physiological deformation; however, the overall effect is lower than the effect with classification symbol 5.

In assessing the state of plants, account shall be taken of the size and size of the plants, of the chlorosis and growth distortions, as well as of the overall appearance of the plants.

In the following tables with the results of the post-emergence activity of the compounds prepared by the process according to the invention, the individual plants are indicated by abbreviations. The following abbreviations are used:

PN Cyperus rotundus L. SE Sesbania exaltata HIM Brassica kaber PI Amaranthus retroflexus RW Ambrosia artemisiifolia MG Ipomea pur.purea BA Echinochloa crusgalli CR Digitaria sanguinalis FO Setaria viridis WO Avena Fatua TW Sida spinosa VL Abutilon threophrasti CN Zea mays WHAT Gossyplum · hirsutum SY Glycine max RI Oryza sativa JW Datura stramonium L.

in

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Dose PN SE MU PI RG MG TW VL BA CR FO WO CN CO SY RI (kg / ha)

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Dose PN SE MU PI RG MG TW VL BA CR FO WO CN CO SY RI (kg / ha)

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Example 9

Preemergence herbicidal activity

The pre-emergence herbicidal activity of the compounds prepared by the process of the invention is determined in this example by testing in which the seeds (or cultivation organs) of certain monocotyledonous and dicotyledonous plants are separately mixed in pots with pots (or planted with pots) ).

A water-acetone solution containing the herbicidally active test compound is then applied to the pots in an amount such that an equivalent of 0.28 to 11.2 kg of active ingredient per hectare is achieved. The pots are then placed in a greenhouse where they are irrigated and otherwise treated in the usual manner.

Three or four weeks after the application of the active compound, the assays are terminated and all plants are evaluated according to the classification system given in Example 8.

The pre-emergence herbicidal activity of the individual test compounds is shown in Tables 5 and 6 below, summarizing the results obtained.

TABLE 5

Preemergence herbicidal activity of the compounds of the formula

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Pre-emergence herbicidal activity of compounds of formula

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Example 10

Selective post-emergence herbicidal activity

The selective post-emergence herbicidal activity of the compounds prepared by the process of the invention is demonstrated by the following tests in which plant species

Sorghum bicolor (L) Woeuch, Triticum Acstivum, cv. Auza and Hordcum vulgare, cv. Steptoe, is exposed to test compounds that are dispersed in aqueous acetone mixtures. These tests were carried out as in Example 8; the plant condition is then also evaluated in the same way. The results obtained are summarized in Table 7 below.

TABLE 7

Selective post-emergence herbicidal activity of the compounds of formula

Ri R2 R3 X Dose (kg / ha) Sorghum Auza Steptoe —СНз —СН (СНз) з —СН2СН2ОСН3 н 2.24 2 5 2 1.12 0 5 0 0.56 0 0 0 СНз —СНз -СН (СНз) 2 —С — С2Н5 н 2.24 2 5 0 | 1.12 0 3 0 СНз 0.56 0 5 0 —СНз —СН (СНз) 2 —СН2СН2ОС2Н5 н 2.24 3 2 2 1Д2 0 2 2 0.56 0 0 0 -СНз —СН (СНз) 2 н 2.24 3 6 3 сн » 1.12 0 5 0 0.56 0 3 0 —СНз —СН (СНз) 2 —Он? —С = н 2.24 2 3 0 = С — С7Н15-П 1.12 0 2 0 0.56 0 2 0 СН (СН ^) —СНз —СН (СНз) г. \ ЭХ н 2.24 0 3 2 Ул 1.12 0 0 0 0.56 0 0 0 X 3 —СНз —СН (СНз) 2 —СНз 4 (5) 2.24 2 1 0 1.12 2 0 0 0.56 0 0 0 —СНз —СН [СНз] 2 -С2Н5 Н 2.24 2 9 2 (+) isomer 1.12 1 8 0 0.56 0 3 0 —СНз —СН (СНз) 2 —СН2 — С = СН 3 (7) С1 2.24 2 0 0 1.12 0 0 0 0.56 0 0 0 —СНз —СН (СНз) 2 —С2Н5 3 (6) -2 2.24 0 0 0 1Д2 0 0 0 0.56 0 0 0

Example 11

Selective pre-emergence herbicidal activity

The selective pre-emergence herbicidal activity of the compounds prepared according to the invention for the plant species Sorghum bicolor (L) Moeuch, Triticum acstivum, cv. Auza and Hordeum vulgare, cv. Steptoe. After the test, the classification system used in Example 8 was used to evaluate the plants. The results obtained are summarized in Table 8 below.

TABLE 8

Selective pre-emergence herbicidal activity of the compounds of formula

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2S

OBJECT OF THE INVENTION

Claims (18)

OBJECT OF THE INVENTION A herbicidal composition, characterized in that it contains, as active ingredient, a compound of the formula (I) in which it is X is hydrogen, alkyl of 1 to 3 carbon atoms, halogen or nitro, R 1 is C 1 -C 4 alkyl, R 2 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, phenyl or benzyl, wherein R 1 and R 2 together with the carbon atom to which they are attached may form a (C 3 -C 6) cycloalkyl group which may be optionally substituted with a methyl group, R 3 is hydrogen, an alkyl group having 1 to 12 carbon atoms which may be optionally substituted by one alkoxy group having 1 to 3 carbon atoms or one cycloalkyl group having 3 to 6 carbon atoms or one phenyl group or one furyl group; 3 to 5 carbon atoms which may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogen substituents, an alkynyl group having 3 to 5 carbon atoms which may optionally be substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogenated tubstituens, benzyl, cyclohexenylmethyl, ethinylcyclohexyl, ethinylallyl or pentadienyl, cycloalkyl having 3 to 6 carbon atoms and having a it may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms or a salt forming a cation consisting of an alkali metal, an ammonium group or an aliphatic ammonium group having a total carbon number of 1 to 18, or its optical isomers and mixtures thereof isomers when R 1 and R 2 have different meanings, or acid addition salts thereof when R 3 is not a salt forming a cation. 2. A herbicidal composition as claimed in claim 1, characterized in that it contains a compound of the formula I as active ingredient, X is hydrogen, alkyl of 1 to 3 carbon atoms, halogen or nitro, R 1 is C 1 -C 4 alkyl, R 2 is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having - R1 and R2 together with the carbon atom to which they are attached may form a cycloalkyl group having 3 to 6 carbon atoms, which may optionally be substituted by a methyl group, R 3 is hydrogen, C 1 -C 12 alkyl, alkenyl 3 to 5 carbon atoms, which may optionally be substituted with one or two methyl groups or one or two halogen substituents, a 3 to 5 carbon alkynyl group which may be optionally substituted with one or two methyl groups or one or two halogen groups substituents, benzyl, cyclohexenylmethyl or - pentadienyl or a cation forming salt of alkali metal, ammonium or aliphatic ammonium - having a total carbon number of 1 to 18, or optical isomers thereof, and mixtures of these optical isomers when R 1 and R 2 have different meanings, or acid addition salts thereof, when R 1 is not a cation forming salt. 3. A herbicidal composition as claimed in claim 1, wherein the active ingredient is a compound of the formula (I): X is hydrogen, methyl, chloro or nithio, R 1 -C 1 -C 3 alkyl, R 2 is C 1 -C 3 alkyl or cyclohexyl, wherein R 1 and R 2 together with the carbon atom to which they are attached may form a cyclohexyl group or a methylcyclohexyl group, R 3 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl which may optionally be substituted by one or two chlorine substituents or one or two C 1 -C 3 alkyl groups, C 3 alkynyl group up to 5 carbon atoms, which may be optionally substituted by one or two alkyl groups having 1 to 3 carbon atoms, benzyl, cyclohexyl, xenylmethyl or pentadienyl, as well as optical isomers and isomeric mixtures thereof when R 1 and R 2 have different meanings, and acid addition salts thereof when R 3 is not a cation forming salt. 4. A herbicidal composition as claimed in claim 2, characterized in that it contains a compound of the formula I as active ingredient in which: X is hydrogen, methyl, chloro or nitro, R 1 is an alkyl group having 1 to 3 carbon atoms, R 2 is C 1 -C 3 alkyl or cyclohexyl, wherein R 1 and R 2 together with the carbon atom to which they are attached may form a cyclohexyl group or a methylcyclohexyl group, R 3 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl optionally substituted by one or two chlorine substituents or one or two methyl groups, C 3 -C 5 alkynyl be optionally substituted with one or two methyl groups, a benzyl group, a cyclohexenylmethyl group or a pentadienyl group, as well as its optical isomers and isomeric mixtures when R 1 and R 2 have different meanings, and its acid addition salts when R 3 is not a salt forming a cation. 5. The herbicidal composition of claim 1 wherein X is hydrogen, methyl or chlorine, R1 is methyl, R2 isopropyl, and R3 is hydrogen, alkyl having 1 to 12 carbon atoms. atoms which may be optionally substituted by one alkyl group having 1 to 3 carbon atoms or one cycloalkyl group having 3 to 6 carbon atoms or one phenyl group or, by one furyl group, an alkenyl group having 3 to 5 carbon atoms which may be optionally substituted one or two alkyl groups having 1 to 3 carbon atoms or one phenyl group or one or two halogen substituents, an alkynyl group having 3 to 5 carbon atoms, which may optionally be substituted by one or two alkyl groups having 1 to 3 carbon atoms or one phenyl or one or more two halogen substituents, benzyl, cyclohexenylmethyl, ethinylcyclohexyl, ethinylallyl or pentadienyl, cycloalkyl of 3 to 6 carbon atoms, which may optionally be substituted by one or two alkyl groups of 1 to 3 carbon atoms, or a salt forming a cation, consisting of an alkali metal, an ammonium group or an aliphatic ammonium group with a total number of carbon atoms · 1 to 18. 6. The herbicidal composition of claim 2, wherein the active ingredient is a compound of formula (I) wherein X is methyl, hydrogen or chlorine, R1 isopropyl, and R3 represents hydrogen, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms which may be optionally substituted by one or two methyl groups or one or two halogen substituents, an alkynyl group having 3 to 5 carbon atoms, which may be optionally substituted by one or two methyl groups or one or two halogen substituents, benzyl, cyclohexenylmethyl or pentadienyl or a salt forming a cation formed by an alkali metal, ammonium or aliphatic ammonium group having a total carbon number of 1 to 18 . 7. The herbicidal composition of claim 2, wherein the active ingredient is 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid 2-propylester. . 8. A herbicidal composition as claimed in claim 2, wherein the active ingredient is 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid methyl ester. 9. The herbicidal composition of claim 2, wherein the active ingredient is 2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid. 10. The herbicidal composition of claim 2, wherein the active ingredient is an isomeric mixture of methyl 6- (5-sopropl15-methyl-4-oxo-2-midazolin-2-yl) m-toluic acid methyl ester and 2- (5 5-methyl-15-methyl-4-oxo-2-midazolin-2-yl] -1'-toluic acid. 11. The herbicidal composition of claim 2, wherein the active ingredient is (+) -2- (5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid ethyl ester. 12. The herbicidal composition of claim 2, wherein the active ingredient is (+) - 2- (5-isoproryl-5-methyl-4-oxo-2-imidazolin-2-yl) benzoic acid 2-chlorallyl ester. 13. A process for the preparation of a compound of formula (I) as claimed in claim 1, wherein it is X is hydrogen, (C 1 -C 3) alkyl, halogen or nitro, R (C 1 -C 4) alkyl, R 2 is a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 2 -C 4 alkenyl group, a phenyl group, a halophenyl group or a benzyl group, wherein R 1 and R 2 together with the carbon atom to which they are attached, to form a C 3 -C 6 cycloalkyl group which may be optionally substituted by a methyl group, R 3 hydrogen, an alkyl group having 1 to 12 carbon atoms which may be optionally substituted by one alkoxy group having 1 to 3 carbon atoms, or one} C 3 -C 6 cycloalkyl or one phenyl or one furyl, C 3 -C 5 alkenyl which may optionally be substituted by one or two C 1 -C 3 alkyl groups or one phenyl group or one or two or more two halogen substituents, alkynyl group a C 3 -C 5 alkyl group which may be optionally substituted by one or two C 1 -C 3 alkyl or one phenyl or one or two halogen substituents, benzyl, cyclohexenylmethyl, ethhnylcyclohexyl, ethinylalkyl or pentadienyl, C 3 -C 6 cycloalkyl, which may be optionally substituted by one or two C 1 -C 3 alkyl groups or a cation-forming alkali metal, ammonium or aliphatic ammonium group having a total carbon number of 1 to 18, as well as and their optical isomers and isomeric mixtures when R 1 and R 2 have different meanings, and their acid addition salts when R 3 is not a cation-forming salt, characterized in that a compound of formula (II) in which R is reacted 3 is as defined above, in the presence of an alkali metal or alkali metal hydride at a temperature of 20 to 50 ° C, whereupon the compound of formula I is optionally converted into an acid addition salt. 14. A process for the preparation of a compound of formula (I) as claimed in claim 2 wherein it is X is hydrogen, alkyl of 1 to 3 carbon atoms, halogen or nitro, R 1 is C 1 -C 4 alkyl, R 2 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, phenyl, halophenyl or benzyl, wherein R 1 and R 2 together with the carbon atom to which they are attached to form a cycloalkyl group having 3 to 6 carbon atoms which may be optionally substituted by a methyl group, R 3 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl optionally substituted by one or two methyl groups or one or two halogen substituents, C 3 -C 5 alkynyl which may be optionally substituted with one or two methyl groups or with one phenyl group or with one or two halogen substituents, benzyl, cyclohexenylmethyl or pentadienyl or a salt forming a cation consisting of an alkali metal, ammonium or aliphatic ammonium group having a total carbon number of 1 to 18, and their optical isomers and isomeric mixtures when R 1 and R 2 have different meanings, and their acid addition salts when R 3 is not a cation-forming salt, characterized in that the compound of formula (II) is reacted in wherein X, R 1 and R 2 are as defined above, with an alcohol of formula R3-OH wherein X, R1 and R2 are as defined above, with an alcohol of formula R 3 -OH, wherein R 3 is as defined above, in the presence of an alkali metal or alkali metal hydride at a temperature of 20 to 50 ° C, whereupon optionally converting a compound of formula I to its acid addition salt. 15. The process of claim 13 wherein the ratio of alcohol to compound of formula II is 1.1: 1 to 5: 1 and the reaction is conducted under an inert gas atmosphere. 16. The process of claim 14 wherein the ratio of alcohol to compound of formula II is 11: 1 to 5: 1 and the reaction is conducted under an inert gas atmosphere. 17. The process of claim 13 wherein an aprotic solvent is added to the reaction mixture of the compound of formula II, an alcohol and an alkali metal or alkali metal hydride such that the aprotic solvent to alcohol ratio does not exceed 4: 1 and the reaction is conducted under an inert atmosphere. gas. 18. The process of claim 14, wherein an aprotic solvent is added to the reaction mixture of the compound of formula II, an alcohol and an alkali metal or alkali metal hydride in an amount such that the aprotic solvent to alcohol ratio does not exceed 4: 1. gas. Scrography, n., Plant 7, Most