DE4035758A1 - New alpha-pyrimidinyl:oxy(thio) and alpha-triazinyl:oxy(thio) carboxylic acids - used as herbicides, fungicides and as plant growth regulators - Google Patents

Abstract

Substd. alpha-pyrimidinyloxy(thio)- and alpha-triazinyloxy(thio)-beta -(hetero)aryl-carboxylic acid derivs. of formula (I) and their alkali(ne earth) metal and (organo)ammonium salts and optically active isomers are new. Where A = CBEF or a gp. of formula (i): where n = 2 or 3; B = a gp. of formula (ii)-(iv): Where E = H, phenyl, 3-8C cycloalkyl, or alkyl, alkenyl or alkynyl (each contg. up to 6 C and each opt. substd. by one or more Q); G = H or R; Q = RO, RS, NH2, NHR, NR2, NO2, halo or phenyl; R = 1-4C alkyl; R1 = H, 1-12C alkyl or 2-12 alkyl (interrupted by one or more O or S atoms), both opt. substd. by OH, halo, RO, RS, 3-6C cycloalkyl, benzyl, furyl, tetrahydrofuryl, phenyl, halophenyl, RO-phenyl, R-phenyl, nitro-phenyl, CN, COOH, R-CO, RNH or R2N; 3-8C alkenyl or 3-8C alkynyl, both opt. substd. by 1-3C alkoxy, halo or phenyl; 3-6 cycloalkyl, methyl (3-6C) cycloalkyl di(1-4C alkyl)methylene imino or 3-6C cycloalkyleneimino; R2, R3 = R, RO, RS, RNH, R2N or halo; R4-R8 = H, R, RO, RS, NH2, RNH, R2N, NO2, halo, 1-4C haloalkyl or phenyl; X = O or S; Y = CH2 or O. Provided that B is not phenyl when E is H or Me. USE/ADVANTAGE - (I) are herbicides useful against broad leaved weeds and grasses. They may be used as defoliants desiccants and weedkillers and can be applied both pre- or post-emergence. Dosage is 0.001-5 kg/ha.

Description

The invention relates to new substituted α-pyrimidinyloxy (thio) - and α-Triazinyloxy (thio) carboxylic acid derivatives, process for their preparation and their use as agents with herbicidal, fungicidal and plant wax regulating effects.

It is already known that certain pyrimidine derivatives have a herbicidal activity own (EP applications 02 23 406, 02 49 707, 02 49 708, 02 87 072, 02 87 079 and 03 47 811). However, the herbicidal activity is frequently known Connections are not sufficient, or occur with the corresponding Herbicidal effects selectivity problems in agricultural Main crops on.

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 α-pyrimidinyloxy (thio) - and α-Triazinyloxy (thio) carboxylic acid derivatives of the general formula I

in the
A is one of groups A-1 or A-2 of the general formula

if B is not simultaneously free phenyl and E is hydrogen or methyl,
or

where n = 2 or 3,
B is one of groups B-1 to B-3 of the general formulas

E is a hydrogen, a C₁-C₆-alkyl radical, one or more, the same or different by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, nitro , Halogen or phenyl substituted C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, one or more, the same or different by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di- C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more, identically or differently by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁ -C₄-alkylamino, di-C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₂-C₆-alkynyl radical, a C₃-C₈-cycloalkyl radical, one or more, the same or different, by C₁-C₄-alkyl, C₁- C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₃-C₆-cyclo alkyl radical, a phenyl radical,
G represents a hydrogen atom or a C₁-C₄ alkyl radical,
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-alkoxyphenyl , C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino or di-C₁-C₄-alkylamino substituted C₁-C₁₂-alkyl radical, a C₂- interrupted by one or more oxygen atoms or sulfur atoms C₁₂-alkyl radical, one 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, carboxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino or di-C₁-C₄-alkylamino substituted C₂-C₁₂-alkyl radical, a C₃-C₈-alkenyl radical, one by C₁-C₃ alkoxy, phenyl or halogen substit uated C₃-C₈-alkenyl, a C₃-C₈-alkynyl, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈-alkynyl, a C₃-C₆-cycloalkyl, a methyl-substituted C₃-C₆-cycloalkyl, one Di-C₁-C₄- alkylmethyleneimino or a C₃-C₆-cycloalkyleneimino,
R² is a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, a C₁-C₄-alkylamino radical, a di-C₁-C₄-alkylamino radical or a halogen atom,
R³ is a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, a C₁-C₄-alkylamino radical, a di-C₁-C₄-alkylamino radical or a halogen atom,
R⁴, R⁵, R⁶, R⁷ and / or R⁸ represent a hydrogen atom, a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, an amino radical, a C₁-C₄-alkylamino radical, a di-C₁- C₄-alkylamino radical, a nitro radical, a halogen atom, a halogen-C₁-C₄-alkyl radical or a phenyl radical,
X is an oxygen atom or a sulfur atom and
Y is a methine group or a nitrogen atom
mean, and their alkali metal salts, alkaline earth metal salts, ammonium salts and organic substituted ammonium salts and their optically active isomers show an interesting herbicidal, fungicidal and plant growth-regulating action.

Preferred compounds of the formula I are those in which
A the group

is where
B for an optionally monosubstituted phenyl ring and
E represents C₁-C₄-alkyl or C₃-C₆-cycloalkyl,
R¹ is hydrogen or C₁-C₄ alkyl,
R² C₁-C₄ alkoxy,
R³ C₁-C₄-alkoxy or C₁-C₄-alkylamino,
X oxygen and
Y nitrogen or the methine group
means.

The term halogen includes fluorine, chlorine, bromine and iodine. Under the label Alkali metal is lithium, sodium and potassium, under the name 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 V represents a halogen atom, an alkylsulfinyl group, an alkylsulfonyl group, a phenylsulfinyl group or a phenylsulfonyl group, with compounds of the general formula III in which A, R¹ 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 A, R¹, R², R³, X and Y have the meanings given under the general formula I, 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 A, R², R³, 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 A, R², R³, M¹, X and Y 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 A, R², R³, X and Y have the meanings given under the general formula I, or
• D) Compounds of the general formula VI in which A, R², R³, X and Y have the meanings given under the general formula I, with a suitable base in a suitable solvent to give a compound of the general formula VII in which A, R², R³, 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, an ammonium or an organically substituted ammonium group, or
• E) Compounds of the general formula VIII in which R², R³, X and Y have the meanings given under general formula I, with a compound of general formula IX in which A and R¹ have the meanings given under the general formula I and Z represents a halogen atom, an alkylsulfonyloxy group or a phenylsulfonyloxy group, in the presence of a suitable solvent and a suitable base, or
• F) a compound of the general formula X in which R¹, R², R³, X and Y have the meanings given under the general formula I, with a compound of the general formula XIA-W (XI) in which A has the meanings given under the general formula I and W for a halogen atom , an alkylsulfonyloxy group or phenyl sulfonyloxy group 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 e.g. B. Example 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.

Process variant A) is preferred in aromatic 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, polar aprotic solvents, such as dimethylformamide, Dimethylacetamide or dimethyl sulfoxide, and in other solvents, such as acetonitrile or water.

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 or potassium carbonate or a metal hydroxide, such as sodium hydroxide or potassium hydroxide can be used.

The reaction is preferably in a temperature range between room temperature and the boiling point of the solvent or solvent mixture carried out. The response time is 1 to 24 hours.

However, the reaction can also take place in the absence of a solvent Temperature range from 120 to 160 ° C, using an alkali metal carbonates, such as anhydrous potassium carbonate.

To produce the α-hydroxy- or α-mercaptocarboxylic acid derivatives can, for example, the following Literature methods are used: J. Org. Chem. 33, 2565 (1968); J. Amer. Chem. Soc. 95: 7146 (1973); J. Chem. Soc. 1957, 3262; J. Org. Chem. 33: 1831 (1968); Can. J. Chem. 60: 2707 (1982); Bull. Soc. Chim. Fr. 1969, 2721; J. Fluorine Chem. 17, 565 (1981); Can. J. Chem. 61, 1397 (1983).  

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 Cal cium carbonate and a metal hydroxide, such as sodium hydroxide or potassium hydroxide, be used.

The temperature range of the reactions 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, or a metal hydroxide such as sodium hydroxide or potassium hydroxide is used will. Ammonia, an alkylamine (primary Amine), a dialkylamine (secondary amine) or a trialkylamine (tertiary Amine) 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), hydrocarbons, such as benzene, toluene or xylene, halogenated hydrocarbons such as methylene chloride or chloroform, 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, aprotic polar solvents such as Di methylformamide, dimethylacetamide or dimethyl sulfoxide and other solvents, such as acetonitrile.

Alkali metals, such as sodium or potassium, alkali metal or Alkaline earth metal hydrides, such as sodium hydride, potassium hydride or calcium hydride, Carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate or potassium hydrogen carbonate, or metal hydrides such as sodium hydroxide or potassium hydroxide 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 24 hours.

The compounds of the general formula IX are described in the literature or can be produced according to processes analogous to the literature: Bull. Soc. Chim. Fr. 1968 (7), 2929; J. Fluorine Chem. 23, 515 (1983); J. Fluorine Chem. 34, 337 (1987); J. Chem. Soc. Perkin Trans. II, 1473 (1987).

Process variant F is preferably used in aprotic solvents, such as benzene, toluene, xylene, tetrahydrofuran, diethyl ether, hexane, dimethylformamide or dimethyl sulfoxide. For deprotonation of the compounds of the general formula X can be bases, such as sodium hydride, potassium tertiary butylate or lithium diisopropylamide can be used.

The reaction temperature is between -78 ° C and the boiling point of respective solvent or solvent mixture. The response time is 0.5 to 24 hours.  

The compounds of the general formula X are described in the literature or can be prepared by the process specified in the literature (Khim. Farm. Zh.) 16 (8), 931-4 (1982); Ukr. Khim. Zh. (Russ. Ed.) 49 (11), 1205-8 (1983); Fizol. Akt. Veshchestva, 18, 75-9 (1986); USSR PS 7 91 746).

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 carbons Hydrogen, such as benzene, toluene and xylene, ethers, such as diethyl ether, Te trahydrofuran and dioxane, carbonitriles, such as acetonitrile, alcohols, such as methanol and ethanol, carboxamides, such as dimethylformamide, and sulfoxides, such as dimethyl sulfoxides.

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 un herb control can be used in annual crops.  

The compounds of the present invention can include, for example, the following Plant genera are used:

Dicot weeds of the genera Sinapis, Lepidium, Galium, Stellria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Ama ranthus, portulaca, xanthium, convolvulus, ipomoea, polygonum, sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, 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 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 currently 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, cyclohexane, 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 of about 100 to 1000 liters / ha. An application of the funds in the so-called low-volume and ultra-low-volume Processes are 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. Ge 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 dodecyl benzenesulfonic acid and nonylphenyl polyoxyethylene

The following examples illustrate the preparation of the invention Links.

Example 1 rac-3-Fluoro-2- (4,6-dimethoxy-2-pyrimidinyloxy) -3-phenylpentanoic acid m-ethyl ester

10 g (44 mmol) of 3-fluoro-2-hydroxy-3-phenylpentanoic acid methyl ester are dissolved in 100 ml of dimethylformamide, and 3.1 g (22 mmol) of potassium carbonate are added. After stirring for 20 minutes, 9.8 g (44 mmol) of 4,6-dimethoxy-2-methylsulfonylpyridine are added to the suspension and the suspension is heated to 80 ° C. for 7 hours. The reaction mixture is poured onto 200 ml of ice water, the precipitated solid is filtered off and recrystallized from diisopropyl ether.
Yield: 9.8 g = 61.1% of theory (mixture of diastereomers 2: 1).
Mp: 112-115 ° C.

Example 2 rac-3-fluoro-2- (4,6-dimethoxy-2-pyridinyloxy) -3-phenylpentanoic acid

5 g (13.7 mmol) of rac-3-fluoro-2- (4,6-dimethoxy-2-pyrimidinyloxy) -3-phenyl pentanoic acid methyl ester according to Example 1 are in 100 ml of methanol / water (1: 1) with 0.76 g (13.7 mmol) of potassium hydroxide were added and the mixture was stirred at room temperature for 24 hours and at 50 ° C. for 8 hours. The reaction solution is added to 200 ml of water and extracted with 100 ml of ethyl acetate. Then the aqueous phase is acidified to pH 2 with hydrochloric acid and extracted three times with 150 ml of ethyl acetate. The combined acetic acid phases are washed with 50 ml of water, dried over magnesium sulfate, filtered and concentrated. The residue is recrystallized from diisopropyl ether.
Yield: 3.7 g = 77.1% of theory (mixture of diastereomers).
Mp .: 175 ° C decomposition.

In an analogous manner, the following compounds of the invention general formula I:

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 an emulsion for this purpose sprayed evenly over the plants with 500 liters of water / ha. Here show the compounds of the invention one 3 weeks after the treatment high crop selectivity in sugar beet (BEAVX) with excellent Effect against weeds. The comparison means did not show the same level Effectiveness and selectivity.

In the following table mean:

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

BEAVX = Beta vulgaris altissima
AVEFA = Avena fatua
BREAD = Bromus tectorum
SETVI = Setaria viridis
SOLSS = Solanum sp.

table

Example B

The plant species listed were in the greenhouse before emergence with the listed compound at a rate of 0.1 kg of active ingredient / ha treated. The compounds were used as an emulsion for this purpose Sprayed 500 liters of water / ha evenly over the plants. Here shows 3 weeks after treatment, the compound of the invention a high Kul Plant selectivity in soybean (GLXMA), cotton (GOSHI) and sunflower (HELAN) with excellent action against weeds. The means of comparison did not show 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

GLXMA = Glycine maxima
GOSHI = Gossypium hirsutum
HELAN = Helianthus annuus
AGRRE = Elymus repens
SETVI = Setaria viridis
POLSS = Polygonum sp.
VERPE = Veronica persica.

table

Example C

The plant species listed were in the greenhouse before emergence with the listed compound at a rate of 0.1 kg of active ingredient / ha treated. The compounds were used as an emulsion for this purpose Sprayed 500 liters of water / ha evenly over the plants. Here shows 3 weeks after treatment, the compound of the invention a high Kul Plant selectivity in maize (ZEAMX) with excellent activity against the weed. The comparative agent did not show 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

ZEAMX = Zea mays
BREAD = Bromus tectorum
ABUTH = Abutilon theophrasti
IPOSS = Ipomoea purpurea
MATCH = Matricaria chamomilla
SOLSS = Solanum sp.
VERPE = Veronica persica

table

Example D

The plant species listed were in the greenhouse before emergence with the listed compound at a rate of 0.1 kg of active ingredient / ha treated. The compounds were used as an emulsion for this purpose sprayed evenly over the plants with 500 liters of water / ha. Here show the compounds of the invention one 2 weeks after the treatment high crop selectivity in sunflower (HELAN) with excellent Effect against weeds. The comparison means did not show the same level Selectivity.

In the following table mean:

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

HELAN = Helianthus annuus
PANSS = Panicium maximum
SOLSS = Solanum sp.

table

Example E

In the greenhouse, the compounds listed in the table with the applied application rates also mentioned. For this, the active ingredient pipetted onto the water surface. ORYSA, ECHCG, SAGPY and SCPJU used in the pre-emergence and in the 1-2 leaf stage. How the table shows, the compounds of the invention are highly effective against EHCG, SAGPY and SCPJU (important rice weeds) and at the same time selective to water rice. The comparison means did not show the same level Effectiveness.

In the following table mean:

0 = no damage
1 = slight damage
2 = moderate damage
3 = severe damage
4 = totally destroyed

ORYSA = Oryza sativa
ECHCG = Echinochloa Crus-galli
SAGPY = Sagittaria pygmaea
SCPJU = Scirpus juncoides

table

Claims (8)

1. Substituted α-pyrimidinyloxy (thio) - and α-triazinyloxy (thio) -β- (hetero) aryl-carboxylic acid derivatives of the general formula I in the
A is one of groups A-1 or A-2 of the general formula if B is not simultaneously free phenyl and E is hydrogen or methyl,
or where n = 2 or 3,
B is one of groups B-1 to B-3 of the general formulas E is a hydrogen, a C₁-C₆-alkyl radical, one or more, the same or different by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, nitro , Halogen or phenyl substituted C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, one or more, the same or different by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di- C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more, identically or differently by C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁ -C₄-alkylamino, di-C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₂-C₆-alkynyl radical, a C₃-C₈-cycloalkyl radical, one or more, the same or different, by C₁-C₄-alkyl, C₁- C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, nitro, halogen or phenyl substituted C₃-C₆-cyclo alkyl radical, a phenyl radical,
G represents a hydrogen atom or a C₁-C₄ alkyl radical,
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-alkoxyphenyl , C₁-C₄-alkoxyphenyl, nitrophenyl, cyano, carboxyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylamino or di-C₁-C₄-alkylamino substituted C₁-C₁₂-alkyl radical, a C₂- interrupted by one or more oxygen or sulfur atoms C₁₂-alkyl radical, one 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-alkyl radical, a C₃-C₈-alkenyl radical, one by C₁-C₃ alkoxy, phenyl or halogen substituted ated C₃-C₈-alkenyl, a C₃-C₈-alkynyl, a C₃-C₃-alkoxy, phenyl or halogen substituted C₃-C₈-alkynyl, a C₃-C₆-cycloalkyl, a methyl-substituted C₃-C₆-cycloalkyl, one Di-C₁-C₄- alkylmethyleneimino or a C₃-C₆-cycloalkyleneimino,
R² is a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, a C₁-C₄-alkylamino radical, a di-C₁-C₄-alkylamino radical or a halogen atom,
R³ is a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, a C₁-C₄-alkylamino radical, a di-C₁-C₄-alkylamino radical or a halogen atom,
R⁴, R⁵, R⁶, R⁷ and / or R⁸ represent a hydrogen atom, a C₁-C₄-alkyl radical, a C₁-C₄-alkoxy radical, a C₁-C₄-alkylthio radical, an amino radical, a C₁-C₄-alkylamino radical, a di-C₁- C₄-alkylamino radical, a nitro radical, a halogen atom, a halogen-C₁-C₄-alkyl radical or a phenyl radical,
X is an oxygen atom or a sulfur atom and
Y is a methine group or an oxygen atom
mean, and their alkali metal salts, alkaline earth metal salts, ammonium salts and organic substituted ammonium salts and their optically active isomers. 2. Substituted -Pyrimidinyloxy (thio) - and -Triazinyloxy (thio) -carboxylic acid derivatives according to Claim 1 of the formula I, in which
A the group is where
B for an optionally monosubstituted phenyl ring and
E represents C₁-C₄ alkyl or C _3-6 cycloalkyl,
R¹ is hydrogen or C _1-4 alkyl,
R² C _1-4 alkoxy,
R³ C _1-4 alkoxy or C _1-4 alkylamino,
X oxygen and
Y nitrogen or the methine group
means. 3. A process for the preparation of compounds of general formula I, 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 V represents a halogen atom, an alkylsulfinyl group, an alkylsulfonyl group, a phenylsulfinyl group or a phenylsulfonyl group, with compounds of the general formula III in which A, R¹ 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 A, R¹, R², R³, X and Y have the meanings given under the general formula I, 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 A, R¹, R², R³, X and Y and have the meanings given under the general formula I, 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 A, R², R³, 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 A, R², R³, M¹, X and Y 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 A, R², R³, X and Y have the meanings given under general formula I, or
• D) Compounds of the general formula VI in which A, R², R³, X and Y have the meanings given under the general formula I, with a suitable base in a suitable solvent to give a compound of the general formula VII in which A, R², R³, 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, an ammonium ion or an organic substituted ammonium group,
• E) Compounds of the general formula VIII in which R², R³, X and Y have the meanings given under general formula I, with a compound of general formula IX in which A and R¹ have the meanings given under the general formula I and Z represents a halogen atom, an alkylsulfonyloxy group or a phenylsulfonyloxy group, in the presence of a suitable solvent and a suitable base, or
• F) a compound of the general formula X in which R¹, R², R³, X and Y have the meanings given under the general formula I, with a compound of the general formula XIA-W (XI) in which A has the meanings given under the general formula I and W for a halogen atom , an alkylsulfonyloxy group or phenyl sulfonyloxy group in a suitable solvent in the presence of a suitable base.

4. Agents with herbicidal, fungicidal and plant growth regulating Effect, characterized by a content of at least one compound according to claim 1.   5. Use of agents according to claim 3 for combating monocotyledons and dicotyledonous weed species in main agricultural crops. 6. Use of agents according to claim 3 for combating a fungal attack in agricultural crops. 7. Use of agents according to claim 3 for influencing the growth of Crops. 8. Process for the preparation of compositions with herbicidal, fungicidal and growth-regulating effect, characterized in that compounds of general formula I according to claim 1 with carrier and / or auxiliaries mixed.