DE4026177A1 - Benzoic acid and nicotinic acid derivs. - contain pyrimidinyl-methyl or substd. tri:azinyl-methyl, useful as herbicides, fungicides and plant growth regulators - Google Patents

Abstract

2-Pyrimidinylmethyl- and 2-triazinylmethyl-benzoic and nicotinic acid derivs. (I) and their alkali metal, alkaline earth metal and ammonium salts are new. In (I) R1 = H; 1-12C alkyl opt. substd. by hydroxy, halogen, 1-4C alkoxy, 1-4C alkylthio, 3-6C cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, 1-4C alkylphenyl, 1-4C alkoxyphenyl, nitrophenyl, cyano, carboxy, 1-4C alkoxycarbonyl, 1-4C alkylamino, di-1-4C alkylamino, tri-1-4C alkylammonium halide, 2-5C alkyleneimino, or di-1-4C alkylmethyleneimino; 2-12C alkyl interrupted by O or S atom(s); 2-12C alkyl interrupted by O or S atom(s) and substd. by hydroxy, halogen, 1-4C alkoxy, 1-4C alkylthio, 3-6C cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, 1-4C alkylphenyl, 1-4C alkoxyphenyl, nitrophenyl, cyano, carboxy, 1-4C alkoxycarbonyl, 1-4C alkylamino or di-1-4C alkylamino; 3-8C alkenyl or 3-8C alkynyl opt. substd. by 1-3C alkoxy, phenyl or halogen; 3-6C cycloalkyl opt. substd. by methyl; di-1-4C alkylmethyleneimino; or 3-6C cycloalkyleneimino; R2, R3 = halogen, 1-4C alkyl opt. substd. by halogen or 1-4C alkoxy, 1-4C alkoxy, 1-4C alkylthio, 1-4C alkylamino or di-1-4C alkylamino; R4, R5 = H, halogen, nitro, cyano, 1-4C alkyl opt. substd. by halogen, 1-4C alkoxy, phenoxy or 1-4C alkoxycarbonyl; R6 = H, halogen or 1-4C alkyl; X, Y = CH or N. USE/ADVANTAGE - Cpds. (I) are herbicides, fungicides and plant growth regulators. Herbicidal use is esp. as defoliants, desiccants, and weedkillers, e.g. in amt.s of 0.001-5 kg/ha.

Description

The invention relates to new substituted 2-pyrimidinylmethyl and 2-triazinylmethylbenzoe and nicotinic acid derivatives, process for their preparation and their use as herbicidal, fungicidal and plant growth-regulating agents Effect.

It is already known that pyrimidine derivatives have a herbicidal action (EP applications 02 23 406, 02 49 707, 02 49 708, 02 87 072 and 02 87 079). However, the herbicidal activity of the known compounds is frequent not sufficient, or occur with a corresponding herbicide effect Selectivity problems in main agricultural crops.

The object of the present invention is to provide new compounds, that do not have these disadvantages and that in their biological Properties are superior to previously known compounds.

It has now been found that substituted 2-pyrimidinylmethyl- and 2-triazinylmethylbenzoe- and nicotinic acid derivatives of the general formula I

in the
R¹ is a hydrogen atom, a C₁-C₁₂-alkyl radical, one by hydroxy, halogen, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₃-C₆-cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, C₁-C₄-alkylphenyl , C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, tri-C₁-C₄-alkylammonium halide, C₂-C₅-alkyleneimino or di-C₁ -C₄-alkylmethyleniminooxy substituted C₁-C₁₂-alkyl radical, a C₂-C₁₂-alkyl radical interrupted by one or more oxygen atoms or sulfur atoms, an interrupted by one or more oxygen atoms or sulfur atoms and by hydroxy, halogen, C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₃-C₆-cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, C₁-C₄-alkylphenyl, C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino, or Di-C₁-C₄-alkylamino substituted C₂-C₁₂-A lkylrest, a C₃-C₈-alkenyl residue, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈-alkenyl residue, a C₃-C₈-alkynyl residue, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈- Alkynyl radical, a C₃-C₆-cycloalkyl radical, a methyl-substituted C₃-C₆-cycloalkyl radical, a di-C₁-C₄-alkylmethyleneimino radical or a C₃-C₆-cycloalkyleneimino radical,
R² is a C₁-C₄-alkyl group, a halogen-C₁-C₄-alkyl group, a C₁-C₄-alkoxy group, a C₁-C₄-alkoxy-C₁-C₄-alkyl group, a C₁-C₄-alkylthio group, a C₁-C₄-alkylamino group , a di-C₁-C₄-alkylamino radical or a halogen atom,
R³ is a C₁-C₄-alkyl group, a halogen-C₁-Crest-alkyl group, a C₁-C₄-alkoxy group, a C₁-C₄-alkoxy-C₁-C₄-alkyl group, a C₁-C₄-alkylthio group, a C₁-C₄-alkylamino group , a di-C₁-C₄-alkylamino radical or a halogen atom,
R⁴ is a hydrogen atom, a C₁-C₄-alkyl radical, a halogen-C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a phenoxy radical, a nitro group, a halogen atom, a nitrile radical or a C₁-C₄-alkoxycarbonyl radical,
R⁵ is a hydrogen atom, a C₁-C₄-alkyl radical, a halogen-C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a phenoxy radical, a nitro group, a halogen atom, a nitrile radical or a C₁-C₄-alkoxycarbonyl radical,
R⁶ is a hydrogen atom, a halogen atom or a C₁-C₄ alkyl radical,
X is a methine group or a nitrogen atom and
Y represents a methine group or a nitrogen atom, and their alkali metal salts, alkaline earth metal salts and organic ammonium salts and their optically active isomers show an interesting herbicidal, fungicidal and plant growth-regulating action.

The halogen relationship includes fluorine, chlorine, bromine and iodine. Under the label Alkali metal is lithium, sodium and potassium, under the designation Alkaline earth metal to understand calcium, strontium and barium.

The compounds of general formula I according to the invention can for example be made by

• A) Compounds of the general formula II in which R², R³ and Y have the meanings given under the general formula I and Z¹ represents a halogen atom, an alkylsulfonyl group or a phenylsulfonyl group, with compounds of the general formula III in which R¹, R⁴, R⁵, R⁶ and X have the meanings given under the general formula I, in a suitable solvent in the presence of a suitable base, or
• B) Compounds of the general formula IV in which R¹, R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I, but R¹ does not represent a hydrogen atom, in a suitable polar solvent with an alkali metal base or an alkaline earth metal base to give compounds of the general Formula V in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I and M¹ represents an alkali metal atom or an equivalent of an alkaline earth metal atom, or
• C) Compounds of the general formula V in which R², R³, R⁴, R⁵, R⁶, M¹ and X have the meanings given under the general formula V, with a suitable acid in a suitable solvent to give compounds of the general formula VI in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I, implemented, or
• D) Compounds of the general formula VI in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under general formula I, with a suitable base in a suitable solvent to give a compound of general formula VII in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I and M² represents an alkali metal atom, an equivalent of an alkaline earth metal atom or an organic ammonium group, or
• E) a compound of the general formula VIII in which R¹, R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under general formula I, with a compound of general formula IXR⁶ - Z² (IX) in R⁶ have the meanings given under general formula I. has and Z² represents a halogen atom, an alkylsulfonyloxy group, a phenylsulfonyloxy group or a group -O-SO₂-O-alkyl, in a suitable solvent in the presence of a suitable base.

The individual process variants are preferably in the presence of a Diluent carried out. For this purpose, everyone can face the solvents used are inert solvents.

Examples of such solvents or diluents are Water, aliphatic, alicyclic and aromatic hydrocarbons, the may each be optionally chlorinated, such as hexane, cyclohexane, Petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, Chloroform, carbon tetrachloride, ethylene chloride and trichlorethylene, Ethers such as diisopropyl ether, dibutyl ether, propylene oxide, dioxane and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, Methyl isopropyl ketone and methyl isobutyl ketone, nitriles such as Acetonitrile and propionitrile, alcohols, such as methanol, Ethanol, isopropanol, butanol and ethylene glycol, esters such as Ethyl acetate and amyl acetate, acid amides such as dimethylformamide  and dimethylacetamide, sulfoxides and sulfones such as dimethyl sulfoxide and sulfolane, and bases such as pyridine.

The presence of a reaction catalyst can be advantageous. As catalysts potassium iodide and onium compounds are suitable, such as quaternary Ammonium, phosphonium and arsonium compounds as well as sulfonium compounds. Also suitable are polyglycol ethers, especially cyclic ones, such as for example 18-crown-6, and tertiary amines such as tributylamine. Preferred compounds are quaternary ammonium compounds, such as Benzyltriethylammonium chloride and tetrabutylammonium bromide.

The reactions can be carried out at the pressure of the environment, albeit they are also carried out at elevated or reduced pressure can be.

For process variant A), aprotic solvents can preferably be used as solvents Solvents such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, Hexane, dimethylformamide or dimethyl sulfoxide can be used.

The bases can be, for example, sodium hydride, potassium tert-butylate or lithium diisopropylamide be used.

The reaction temperature is between -78 ° C and the boiling point of respective solvent or solvent mixture.

The reaction time is 5 minutes to 48 hours, preferably 0.5 to 24 Hours.

The compounds of the general formula II are described in the literature, or can be produced according to processes analogous to the literature.

Process variants B) and C) are preferred in alcohols, such as methanol, Ethanol or isopropanol, in ketones, such as acetone or methyl ketones, in water or in a mixture of water and a polar solvent carried out.  

A carbonate such as sodium carbonate, potassium carbonate or calcium carbonate can be used as the base and a metal hydroxide such as sodium hydroxide or potassium hydroxide, be used.

The temperature range of the reaction is between room temperature and Boiling point of the respective solvent or solvent mixture. The Response time is 0.5 to 36 hours.

If R¹ in the general formula IV represents a benzyl group, one can Compound of the general formula VI also by catalytic reduction (hydrogenation) be preserved.

For process variant D), hydrocarbons, such as benzene, toluene or xylene, halogenated hydrocarbons such as methylene chloride or chloroform, alcohols, such as methanol, ethanol or isopropanol, Ethers, such as ethyl ether, isopropyl ether, tetrahydrofuran or 1,4-dioxane, Ketones such as acetone or methyl ethyl ketone, esters such as methyl acetate or ethyl acetate, or nitriles such as acetonitrile can be used.

An alkali metal such as sodium or potassium, an alkali metal or alkaline earth metal hydride, such as sodium hydride, potassium hydride or calcium hydride, a carbonate, such as sodium carbonate, potassium carbonate or calcium carbonate, a metal hydroxide, such as sodium hydroxide or potassium hydroxide, or ammonia be used. An alkylamine (primary Amine), a dialkylamine (secondary amine), a trialkylamine (tertiary Amine) or pyridine can be used.

The temperature range of the reaction is between room temperature and Boiling point of the respective solvent or solvent mixture. The Response time is 5 minutes to 10 hours.

For process variant E), aprotic solvents can preferably be used as solvents Solvents such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, Hexane, dimethylformamide or dimethyl sulfoxide can be used.

The bases can be, for example, sodium hydride, potassium tert-butylate or lithium diisopropylamide be used.  

The reaction temperature is between -78 ° C and the boiling point of respective solvent or solvent mixture.

The response time is 1 to 24 hours.

The compounds according to the invention produced by the abovementioned processes can be isolated from the reaction mixture by the customary methods be, for example by distilling off the solvent used at normal or reduced pressure, through precipitation with water or by extraction.

An increased degree of purity can usually be determined by column chromatography Purification and by fractional distillation or crystallization be preserved.

The compounds according to the invention are generally colorless and odorless Liquids, as well as crystals, are soluble in water, slightly soluble in aliphatic hydrocarbons, such as petroleum ether, hexane, pentane and cyclohexane, readily soluble in halogenated hydrocarbons, such as Chloroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons, such as benzene, toluene and xylene, ethers such as diethyl ether, tetrahydrofuran and dioxane, carbonitriles, such as acetonitrile, alcohols, such as methanol and ethanol, carboxamides, such as dimethylformamide, and sulfoxides, such as dimethyl sulfoxide.

The compounds according to the invention show a good herbicidal activity broad-leaved weeds and grasses. A selective use of the invention Active ingredients are possible in different cultures, for example in rapeseed, beets, soybeans, cotton, rice, barley, wheat and other cereals. Individual active ingredients are selective herbicides in beets, Cotton, soybeans and cereals are particularly suitable. Likewise, the connections for weed control in permanent crops, such as forestry, Ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, Oil palm, cocoa, berry fruit and hop plants, and for selective weed control be used in annual crops.  

The compounds of the invention can be used, for example, in the following plant genera:
Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirschum, Carduanus, Carduan Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea and Chrysanthemum.

Monocot weeds of the genera Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Eleocharis, Ischaemum and Apera.

Depending on the type of application, the application rates fluctuate in the pre- and post-emergence between 0.001 and 5 kg / ha.

The active compounds according to the invention can also be used as defoliants, desiccants and can be used as an herbicide. They also affect plant growth and can therefore influence the growth of crops be used. Some of these active ingredients also show a fungicidal effect Effect.

The compounds according to the invention can either be used alone or in a mixture with one another or with other active ingredients. Possibly other pesticides or pesticides may vary depending on the desired purpose can be added. If a broadening of the spectrum of activity other herbicides may also be added. For example, those suitable as herbicidally active mixture partners Active ingredients described in Weed Abstracts, Vol. 39, No. 1, 1990, under the title "List of common names and abbreviations employed for currentyl used herbicides and plant growth regulators in Weed Abstracts ".

A promotion of the intensity and speed of action can Example by adding additives, such as organic solvents, Wetting agents and oils can be achieved. Such additives may therefore be left out a reduction in drug dosage.  

The labeled active ingredients or their mixtures are expediently in Form of preparations, such as powders, sprinkling agents, granules, solutions, Emulsions or suspensions, with the addition of liquid and / or solid Carriers or diluents and, if necessary, adhesives, Wetting, emulsifying and / or dispersing aids applied.

Suitable liquid carriers are, for example, aliphatic and aromatic Hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, Dimethyl sulfoxide, dimethylformamide, mineral oil fractions and Vegetable oils.

Minerals are suitable as solid carriers, for example bentonite, silica gel, Talc, kaolin, attapulgite, limestone, and herbal products, for Example flour.

Examples of surface-active substances include calcium lignin sulfonate, Polyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, Phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates as well as substituted benzenesulfonic acids and their salts.

The proportion of the active ingredient (s) in the different preparations can vary widely. For example, the Average about 10 to 90 percent by weight of active ingredient, about 90 to 10 percent by weight liquid or solid carriers and optionally up to 20 percent by weight surfactants.

The funds can be applied in the customary manner, for example with water as a carrier in spray liquor quantities about 100 to 1000 liters / ha. A Use of the funds in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.

These preparations can be prepared in a manner known per se, for example by grinding or mixing processes. If desired, preparations of the individual components can also be made only briefly be mixed before use, for example in the so-called Tank mix procedure is carried out in practice.  

For the preparation of the various preparations, for example following components:

A) wettable powder
1.)
25 percent by weight of active ingredient
60 weight percent kaolin
10 weight percent silica
5 percent by weight of a mixture of the calcium salt of lignosulfonic acid and the sodium salt of N-methyl-N-oleyl-taurine

2.)
40 percent by weight of active ingredient
25% by weight of clay minerals
25 weight percent silica
10 percent by weight of a mixture of the calcium salt of lignin sulfonic acid and alkylphenyl polyglycol ethers

B) paste
45 percent by weight of active ingredient
5% by weight sodium aluminum silicate
15 percent by weight cetyl polyglycol ether with 8 moles of ethylene oxide
2% by weight spindle oil
10% by weight polyethylene glycol
23 weight percent water

C) Emulsion concentrate
25 percent by weight of active ingredient
15 weight percent cyclohexanone
55% by weight xylene
5 percent by weight of a mixture of the calcium salt of dodecylbenzenesulfonic acid and nonylphenylpolyoxyethylene

The following examples illustrate the preparation of the invention Links:

example 1 2 - [(4,6-Dimethoxypyrimidin-2-yl) methyl] nicotinic acid

27.3 ml (189 mmol) of diisopropylamine are placed in 500 ml of tetrahydrofuran Nitrogen atmosphere at -60 ° C with 72.7 ml (182 mmol) 2.5 M butyllithium, dissolved in hexane, added. The mixture is stirred for 30 minutes and at -60 ° C. 10 g (73 mmol) of 2-methyl-nicotinic acid are then added in portions. The mixture is allowed to come to 0 ° C. in the course of 1 hour and 18.2 g (83 mmol) are added. Add 4,6-dimethoxy-2-methylsulfonylpyrimidine in portions. The reaction mixture is stirred for 48 hours at room temperature and then with saturated Washed ammonium chloride solution. The aqueous phase is 5 N Hydrochloric acid adjusted to pH 5 and extracted several times with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated. The solid obtained is recrystallized from ether.

Yield: 3.5 g = 18% of theory
Mp .: 189-191 ° C (decomposition)

Example 2 2 - [(4,6-Dimethoxypyrimidin-2-yl) methyl] nicotinic acid methyl ester

3 g (10.9 mmol) of 2 - [(4,6-dimethoxypyrimidin-2-yl) methyl] nicotinic acid together with 0.76 g (5.5 mmol) potassium carbonate and 0.75 ml (12 mmol) Methyl iodide dissolved in 30 ml of dimethylformamide and 10 hours at room temperature touched. The reaction mixture is poured onto water, with sodium chloride saturated and extracted three times with ethyl acetate. The organic Phase is washed once with saturated sodium chloride solution, over Magnesium sulfate dried and concentrated. The raw product will eventually on silica gel with hexane / ethyl acetate mixtures (20 to 35% ethyl acetate).

Yield: 2.1 g = 67% of theory
Mp .: 87-88 ° C

Example 3 2 - [(4,6-Dimethoxypyrimidin-2-yl) bromomethyl] nicotinic acid methyl ester -

4 g (13.8 mmol) of methyl 2 - [(4,6-dimethoxypyrimidin-2-yl) methyl] nicotinate be with 200 ml carbon tetrachloride under a nitrogen atmosphere heated to boiling. 2.63 g (15 mmol) of N-bromosuccinimide are added in portions added and refluxed for three hours. Allow to cool filtered and concentrated. The crude product obtained is on silica gel Hexane / ethyl acetate mixtures (20 to 35% ethyl acetate) cleaned.

Yield: 4 g = 79% of theory
Mp .: 105-107 ° C

The following compounds according to the invention were also used in an analogous manner of the general formula I prepared.

The following examples explain the possible uses of the invention Links:

Example A

The plant species listed were in the greenhouse before emergence with the listed compounds at a rate of 0.1 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose or suspensions with 500 liters of water / ha sprayed evenly over the soil. Here three weeks after the treatment showed the invention Compounds a high crop selectivity in wheat and corn excellent action against weeds. The comparative showed not the same effectiveness.

In the following table mean:

0 = no damage
1 = 1 - 24% damage
2 = 25 - 74% damage
3 = 75 - 89% damage
4 = 90 - 100% damage

TRZAK = Triticum aestivum
ZEAMX = Zea mays
SORHA = Sorghum halepense
CYPES = Cyperus esculentus
ABUTH = Abutilon theophrasti
GALAP = Galium aparine
MATCH = Matricaria chamomilla
POLSS = Polygonum sp.
SEBEX = Sesbania exaltata
SOLSS = Solanum sp.

Example B

The plant species listed were in the greenhouse after emergence with the listed compounds at a rate of 0.3 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose or suspensions with 500 liters of water / ha evenly over the plants sprayed. Here two weeks after the treatment showed the inventive Compounds a high crop selectivity in cotton excellent action against weeds. The comparative showed not the same effectiveness.

In the following table mean:

0 = no damage
1 = 1 - 24% damage
2 = 25 - 74% damage
3 = 75 - 89% damage
4 = 90 - 100% damage

GOSHI = Gossypium hirsutum
ALOMY = Alopecurus myosuroides
BREAD = Bromus tectorum
SORHA = Sorghum halepense
ABUTH = Abutilon theophrasti
GALAP = Galium aparine
MATCH = Matricaria chamomilla
POLSS = Polygunum sp.
SEBEX = Sesbania exaltata
SOLSS = Solanum sp.
VERPE = Veronica persica

Claims (7)

1. Substituted 2-pyrimidinylmethyl and 2-triazinylmethylbenzoic and nicotinic acid derivatives of the general formula I in the
R¹ is a hydrogen atom, a C₁-C₁₂-alkyl radical, one by hydroxy, halogen, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₃-C₆-cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, C₁-C₄-alkylphenyl , C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, tri-C₁-C₄-alkylammonium halide, C₂-C₅-alkyleneimino or di-C₁ -C₄-alkylmethyleniminooxy substituted C₁-C₁₂-alkyl radical, a C₂-C₁₂-alkyl radical interrupted by one or more oxygen atoms or sulfur atoms, an interrupted by one or more oxygen atoms or sulfur atoms and by hydroxy, halogen, C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₃-C₆-cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, C₁-C₄-alkylphenyl, C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino, or Di-C₁-C₄-alkylamino substituted C₂-C₁₂-A lkylrest, a C₃-C₈-alkenyl residue, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈-alkenyl residue, a C₃-C₈-alkynyl residue, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈- Alkynyl radical, a C₃-C₆-cycloalkyl radical, a methyl-substituted C₃-C₆-cycloalkyl radical, a di-C₁-C₄-alkylmethyleneimino radical or a C₃-C₆-cycloalkyleneimino radical,
R² is a C₁-C₄-alkyl group, a halogen-C₁-C₄-alkyl group, a C₁-C₄-alkoxy group, a C₁-C₄-alkoxy-C₁-C₄-alkyl group, a C₁-C₄-alkylthio group, a C₁-C₄-alkylamino group , a di-C₁-C₄-alkylamino radical or a halogen atom,
R³ is a C₁-C₄-alkyl group, a halogen-C₁-Crest-alkyl group, a C₁-C₄-alkoxy group, a C₁-C₄-alkoxy-C₁-C₄-alkyl group, a C₁-C₄-alkylthio group, a C₁-C₄-alkylamino group , a di-C₁-C₄-alkylamino radical or a halogen atom,
R⁴ is a hydrogen atom, a C₁-C₄-alkyl radical, a halogen-C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a phenoxy radical, a nitro group, a halogen atom, a nitrile radical or a C₁-C₄-alkoxycarbonyl radical,
R⁵ is a hydrogen atom, a C₁-C₄-alkyl radical, a halogen-C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a phenoxy radical, a nitro group, a halogen atom, a nitrile radical or a C₁-C₄-alkoxycarbonyl radical,
R⁶ is a hydrogen atom, a halogen atom or a C₁-C₄ alkyl radical,
X is a methine group or a nitrogen atom and
Y represents a methine group or a nitrogen atom, and also their alkali metal salts, alkaline earth metal salts and organic ammonium salts and their optically active isomers. 2. A process for the preparation of compounds of general formula I according to claim 1, characterized in that

• A) Compounds of the general formula II in which R², R³ and Y have the meanings given under the general formula I and Z¹ represents a halogen atom, an alkylsulfonyl group or a phenylsulfonyl group, with compounds of the general formula III in which R¹, R⁴, R⁵, R⁶ and X have the meanings given under the general formula I, in a suitable solvent in the presence of a suitable base, or
• B) Compounds of the general formula IV in which R¹, R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I, but R¹ does not represent a hydrogen atom, in a suitable polar solvent with an alkali metal base or an alkaline earth metal base to give compounds of the general Formula V in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I and M¹ represents an alkali metal atom or an equivalent of an alkaline earth metal atom, or
• C) Compounds of the general formula V in which R², R³, R⁴, R⁵, R⁶, M¹ and X have the meanings given under the general formula V, with a suitable acid in a suitable solvent to give compounds of the general formula VI in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I, implemented, or
• D) Compounds of the general formula VI in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under general formula I, with a suitable base in a suitable solvent to give a compound of general formula VII in which R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I and M² represents an alkali metal atom, an equivalent of an alkaline earth metal atom or an organic ammonium group, or
• E) a compound of the general formula VIII in which R¹, R², R³, R⁴, R⁵, R⁶, X and Y have the meanings given under the general formula I, with a compound of the general formula IXR⁶ - Z² (IX) in the R⁶ have the meanings given under the general formula I. has and Z² represents a halogen atom, an alkylsulfonyloxy group, a phenylsulfonyloxy group or a group -O-SO₂-O-alkyl, in a suitable solvent in the presence of a suitable base.

3. Agents with herbicidal, fungicidal and plant growth regulating Effect, characterized by a content of at least one compound according to claim 1. 4. Use of agents according to claim 3 for combating monocotyledons and dicotyledonous weed species in main agricultural crops. 5. Use of agents according to claim 3 for combating a fungal attack in agricultural crops. 6. Use of agents according to claim 3 for influencing the growth of Crops.   7. Process for the preparation of herbicidal, fungicidal and growth-regulating effect, characterized in that compounds of general formula I according to claim 1 with carrier and / or Auxiliary materials mixed.