WO1999007698A1

WO1999007698A1 - (hetero)aryloxypyrazoles used as herbicides

Info

Publication number: WO1999007698A1
Application number: PCT/EP1998/004730
Authority: WO
Inventors: Karl-Heinz Linker; Joachim Kluth; Markus Dollinger
Original assignee: Bayer Aktiengesellschaft
Priority date: 1997-08-11
Filing date: 1998-07-29
Publication date: 1999-02-18
Also published as: AU9070798A; DE19734664A1

Abstract

The invention relates to (hetero)aryloxypyrazoles with general formula (I), in which the radicals R1 to R5 have the meanings given in the description. The invention also relates to a method for their production and their use as herbicides.

Description

(HETERO) ARYLOXYPYRAZO E AS HERBICIDES

The invention relates to new (hetero) aryloxypyrazoles, a process for their preparation and their use as herbicides.

Some (hetero) aryloxypyrazoles are already known from the (patent) literature (cf. EP-A-295233, WO-A-93/04044). However, these connections have so far not gained any particular importance.

The new (hetero) aryloxypyrazoles of the general formula (I) have now been found

in which

A represents nitrogen or the groups C-H or C-halogen,

Rl represents cyano or haloalkyl,

R. represents hydrogen, cyano or halogen,

R.3 represents hydrogen, halogen or in each case optionally substituted alkyl or alkoxy,

R4 stands for cyano or the grouping -CO-R ^, R ^ represents hydrogen or optionally substituted alkyl,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ^{7 represents} hydrogen or optionally substituted alkyl, alkenyl,

Is alkynyl or cycloalkyl,

R ^{8 represents} hydrogen or represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and

R ^{9 has} the same meaning as R ⁸ , but without being identical to R ⁸ in each individual case, or together with R ^{8 represents} alkanediyl which may be interrupted by oxygen.

The invention preferably relates to compounds of the formula (I) in which

A represents nitrogen or the groups C-H, C-F or C-Cl,

R * represents cyano or alkyl having 1 to 6 carbon atoms substituted by fluorine and / or chlorine,

R ^ represents hydrogen, cyano, fluorine, chlorine or bromine,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 6 carbon atoms,

R ^ stands for cyano or the grouping -CO-R ", R ^ represents hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by fluorine and / or chlorine,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ^{7 represents} hydrogen, in each case optionally substituted by fluorine and / or chlorine alkyl, alkenyl or alkynyl each having up to 6 carbon atoms or by cycloalkyl optionally having fluorine, chlorine and / or methyl having 3 to 6 carbon atoms,

R ⁸ for hydrogen, for optionally substituted by fluorine, chlorine, methoxy or ethoxy alkyl with 1 to 6 carbon atoms, for each optionally substituted by fluorine and / or chlorine alkenyl or alkynyl each with 2 to 6 carbon atoms, for each optionally substituted by fluorine, chlorine and / or methyl substituted cycloalkyl or cycloalkylalkyl with 3 to 6

Carbon atoms in the cycloalkyl group and optionally 1 or 2 carbon atoms in the alkyl part, for each optionally by nitro, cyano, fluorine, chlorine, bromine, Cj-C4-alkyl, Cj-C / j-haloalkyl, C1 -C4 alkoxy or C1 -C4 -Halogenalkoxy substituted aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 or 2

Carbon atoms in the alkyl part, or for heterocyclyl or heterocyclicalkyl or heterocyclicalkyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, C1-C4-alkyl, -C-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy Series oxetanyl, furyl, tetrahydrofüryl, furylmethyl, tetrahydrofürylmethyl, thienyl, thienylmethyl, pyrazolyl, pyrazolylmethyl, pyridyl,

Pyridylmethyl, pyrimidyl or pyrimidylmethyl, and

R ^{9 has} the same meaning as R ⁸ , but without being identical to R ⁸ in each individual case, or together with R ^{8 represents} alkanediyl having 2 to 6 carbon atoms which may be interrupted by oxygen.

The invention relates in particular to compounds of the formula (I) in which A represents nitrogen or the groups CH, CF or C-Cl,

Rl represents cyano or trifluoromethyl,

R2 represents hydrogen, cyano, fluorine, chlorine or bromine,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n-, each optionally substituted by fluorine and / or chlorine. or i-propoxy,

R4 stands for cyano or the grouping -CO-R °,

R5 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ⁷ for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl optionally substituted by fluorine and / or chlorine,

Butenyl, propynyl or butynyl, or for each optionally by fluorine,

Chlorine and / or methyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

R ⁸ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine and / or chlorine Propenyl, butenyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine and / or methyl, each optionally substituted by nitro, cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or benzyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series oxetanyl, furyl, tetrahydrofuryl, furylmethyl, tetrahydrofrylmethyl, thienyl, thienyl, thazyl, thazyl Pyrazolylmethyl, pyridyl, pyridylmethyl, pyrimidyl or pyrimidylmethyl, and

R ^{9 has} the same meaning as R ⁸ , but without being identical to R ⁸ in each individual case, or together with R ⁸ for ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene), Butane-1,4-diyl, (tetramethylene), pentane-1,5-diyl (pentamethylene), hexane-1,6-diyl (hexamethylene) or 3-oxapentane-1,5-diyl.

In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new (hetero) aryloxypyrazoles of the general formula (I) are notable for strong and selective herbicidal activity.

The new (hetero) aryloxypyrazoles of the general formula (I) are obtained if halogen compounds of the general formula (II)

in which

Rl and R ^ have the meaning given above and

X represents halogen,

with hydroxypyrazoles of the general formula (III)

in which

R ³ , R ^ and R ^ have the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

If, for example, 3,5-dichloro-4-fluoro-benzotrifluoride and 5-hydroxy-l-isopropyl-pyrazole-3-carboxylic acid ethyl ester are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

The halogen compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II). In the formula (II), R ^ and R ^ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R * and R ^; X preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Fluorine Chem. 30 (1985), 251-258; J. Heterocycl. Chem. 28 (1991), 971-976).

Formula (III) provides a general definition of the hydroxypyrazoles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In the formula (III), R ³ , R4 and R ^ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ³ , R ^ and R ^ were specified.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. Chem. Ber. 109 (1976), 253-260; loc. Cit. 112 (1979), 1712-1716; loc. cit. 116 (1983), 1525-1530; DE-A-22 19 484).

The reaction auxiliaries for the process according to the invention for the preparation of compounds of the general formula (I) are generally the usual organic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N- Dimethylbenzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5- Dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5- Diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] undec-7-ene

(DBU).

Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated

Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica,

Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita

Monocotyledonous weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharisemumum, Scirpum Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera

Monocot cultures of the genera Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium

However, the use of the active compounds according to the invention is by no means limited to these

Genera limited, but extends in the same way to other plants

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental wood, fruit, wine , Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture fields and for selective weed control in annual crops

The compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, Powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid

Carriers, where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as

Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and

Methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium),

Ametryne, Amidochlor, Amidosulfüron, Asulam, Atrazine, Azimsulfüron, Benazolin,

Benfuresate, bensulfüron (-methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bromobutide, bromofenoxim, bromoxynil, butachlor, butylates,

Cafenstrole, carbetamide, chlomethoxyfen, chloramben, chloridazon, chlorimuron (- ethyl), chloronitrofen, chlorsulfuron, chlortoluron, cinmethylin, cinosulfüron,

Clethodim, Clodinafop (-propargyl), Clomazone, Clopyralid, Clopyrasulfüron, Clor-ansulam (-methyl), Cumyluron, Cyanazines, Cycloate, Cyclosulfamuron, Cycloxydim,

Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dimefüron, Dimepiperate, Dimethachlor, Di- methametryn, dimethenamid, dinitramine, diphenamide, diquat, dithiopyr, diuron,

Dymron, EPTC, Esprocarb, Ethalfluralin, Ethametsulfüron (-methyl), Ethofümesate,

Ethoxyfen, etobenzanide, fenoxaprop (-ethyl), flamprop (-isopropyl), flamprop (-iso- propyl-L), flamprop (-methyl), flazasulfüron, fluazifop (-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, fluren , Fluridone, Fluroxypyr, Flurprimidol, Flurtamone, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Hexazinone, Imazamethabenz (- methyl), Imazamethapyr, Imazamazethoxap, Imaz , Imazosulfon, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Mobloruronuronurol, Metobromuronuronurol, Metobromuronuronurol, Metobromuronuronulol (-methyl), molinates, monolinuron, naproanilides,

Napropamide, Neburon, Nicosulf ron, Norflurazon Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phenmedipham, Piperophos, Pretilachlor, Primisulfüron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafarbide, Prosulfonafide, Prosulfon Pyrazosulfüron (-ethyl), Pyrazoxyfen, Pyributicarb, Pyridate, Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quizalofop (- ethyl), Quizalofop (-p-tefüryl), Rimsulfuron, Sethoxydim, Simazine, Simetrynent, Sulrazone, Sulfione, Trione Sulfometuron (-methyl), sulfosate, tebutam, tebuthiuron, terbuthylazine, terbutryn, thenylchlor, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasuronuron, triasuronuron Triclopyr, Tridiphane, Trifluralin and Triflusulfüron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, spraying or scattering. The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Manufacture examples:

example 1

2.6 g (15 mmol) of 5-hydroxy-l-methyl-pyrazole-3-carboxylic acid ethyl ester are stirred with 2.2 g (16 mmol) of potassium carbonate in 50 ml of dimethyl sulfoxide at room temperature (approx. 25 ° C.) for 10 minutes , then mixed with 3.5 g (16 mmol) of 2,3-dichloro-5-trifluoromethylpyridine and then stirred at 80 ° C. for 2 hours. After cooling to room temperature, the mixture is concentrated in a water jet vacuum, the residue is stirred with water and concentrated. Acidified hydrochloric acid and the crystalline product isolated by suction.

5.4 g (97% of theory) of ethyl 5- (3-chloro-4-trifluoromethyl-pyridin-2-yl-oxy) -l-methyl-pyrazole-3-carboxylate with a melting point of 103 ° C. are obtained.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, the compounds of the formula (I) listed in Table 1 below can also be prepared, for example.

Table 1: Examples of the compounds of the formula (I)

Application examples

Example A

Pre-emergence test

Solvent 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the active ingredient preparation. The amount of water per unit area is expediently kept constant. The active ingredient concentration in the preparation is irrelevant, the decisive factor is only the amount of active ingredient per unit area

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control

0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 2, 6, 7 and 20, with good tolerability to crop plants, such as cotton and corn, in part, show a strong action against weeds Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Example 2 show

6, 8 and 20 with partially good tolerance to crop plants, such as Wheat and sugar beet, effective against weeds.

Claims

claims

1. (hetero) aryloxypyrazoles of the general formula (I)

in which

A represents nitrogen or the groups C-H or C-halogen,

R * represents cyano or haloalkyl,

R2 represents hydrogen, cyano or halogen,

R ^{3 represents} hydrogen, halogen or in each case optionally substituted alkyl or alkoxy,

R4 stands for cyano or the grouping -CO-R ^,

R5 represents hydrogen or optionally substituted alkyl,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ^{7 represents} hydrogen or optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, R ^{8 represents} hydrogen or represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclic or heterocyclylalkyl, and

R ^{9 has} the same meaning as R ⁸ , but without in every individual case

R ^{8 is} identical, or together with R ^{8 represents} alkanediyl which may be interrupted by oxygen.

2. (hetero) aryloxypyrazoles of the general formula (I) according to claim 1, characterized in that

A represents nitrogen or the groups C-H, C-F or C-Cl,

Rl stands for cyano or for alkyl and 1 to 6 carbon atoms substituted by fluorine and / or chlorine,

R ^ represents hydrogen, cyano, fluorine, chlorine or bromine,

R ³ for hydrogen, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine alkyl or alkoxy each having 1 to

6 carbon atoms,

R ^ stands for cyano or the grouping -CO-R ^,

R5 represents hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by fluorine and / or chlorine,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ⁷ for hydrogen, for alkyl, alkenyl or alkynyl each optionally substituted by fluorine and / or chlorine, each having up to 6 carbon atoms. atoms or represents cycloalkyl having 3 to 6 carbon atoms optionally substituted by fluorine, chlorine and / or methyl,

R ⁸ for hydrogen, for alkyl with 1 to 6 carbon atoms optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each alkenyl or alkynyl optionally substituted by fluorine and / or chlorine each having 2 to 6 carbon atoms, for each optionally substituted by fluorine, chlorine and / or methyl-substituted cycloalkyl or cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 or 2 carbon atoms in the alkyl part, for in each case optionally by nitro, cyano, fluorine, chlorine, bromine, Ci - C4-alkyl, C i -C4- Haloalkyl, C _] -C4-alkoxy or -C-C4-haloalkoxy substituted aryl or arylalkyl with 6 or 10 carbon atoms in the aryl group and optionally 1 or 2 carbon atoms in the alkyl part, or for each optionally by nitro,

Cyano, fluorine, chlorine, bromine, C1-C4-alkyl, -C-C4-haloalkyl, Ci - C4 ~ alkoxy or -C-C4-haloalkoxy substituted heterocyclyl or heterocyclylalkyl from the series oxetanyl, furyl, tetrahydrofryl, furylmethyl, tetrahydrofurylmethyl, thienyl , Thienylmethyl, pyrazolyl, pyrazolylmethyl, pyridyl, pyridylmethyl, pyrimidyl or pyrimidylmethyl, and

R ^{9 has} the same meaning as R ⁸ , but without in every individual case

R ^{8 is} identical, or together with R ^{8 stands} for alkanediyl having 2 to 6 carbon atoms which may be interrupted by oxygen.

3. (hetero) aryloxypyrazoles of the general formula (I) according to claim 1, characterized in that

represents nitrogen or the groups CH, CF or C-Cl, Rl represents cyano or trifluoromethyl,

R ^ represents hydrogen, cyano, fluorine, chlorine or bromine,

R- for hydrogen, fluorine, chlorine, bromine or in each case optionally by

Fluorine and / or chlorine substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,

R4 stands for cyano or the grouping -CO-R ^,

R ^ stands for hydrogen or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine,

R ^{6 represents} the groupings -OR ⁷ or -N (R ⁸ R ⁹ ),

R ⁷ for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine,

Propenyl, butenyl, propynyl or butynyl, or for cyclopropyl optionally substituted by fluorine, chlorine and / or methyl,

Cyclobutyl, cyclopentyl or cyclohexyl,

R ⁸ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine and / or chlorine Propenyl, butenyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine and / or methyl, each optionally by nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoro- methoxy substituted phenyl or benzyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series oxetanyl, furyl,

Tetrahydrofüryl, furylmethyl, tetrahydrofurylmethyl, thienyl, thienylmethyl, pyrazolyl, pyrazolylmethyl, pyridyl, pyridylmethyl, pyrimidyl or pyrimidylmethyl, and

R ^{9 has} the same meaning as R ⁸ , but without in every individual case

R ^{8 be} identical, or together with R ⁸ for ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene), butane-1,

4-diyl, (tetramethylene), pentane-1,5-diyl (pentamethylene), hexane-1,6-diyl (hexamethylene) or 3-oxapentane-1,5-diyl.

A process for the preparation of (hetero) aryloxypyrazoles of the general formula (I) according to claim 1, characterized by reacting halogen compounds of the general formula (II)

in which

Rl and R ^ have the meaning given in claim 1 and

X represents halogen,

with hydroxypyrazoles of the general formula (III)

in which

R-, R4 and R ^ have the meaning given in claim 1,

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.

5. Use of at least one (hetero) aryloxypyrazole according to one of claims 1 to 3 for combating undesirable plants.

6. Herbicidal agent, characterized by the content of at least one (hetero) aryloxypyrazole according to one of claims 1 to 3.