Simple cyclohexanedione esters and herbicide composition

 

(57) Abstract:

Simple cyclohexanedione esters of the formula I, where n = 0 to 2; R1- C1- C6-alkyl; R2- C1- C4-alkyl; A - C1- C4- alkalinity or C3- C6- alkenilovyh bridge, and each of these bridges may be substituted by 1 to 3 C1- C3-alkilani, or WITH3- C6-Allenova the bridge one methylene group may be replaced by oxygen atom; Z is phenyl, isoxazolyl, thienyl; X is halogen or C1- C4-alkyl, can find application in agriculture, namely herbicide compositions on their basis. Structure formula

2 S. p. f-crystals, 8 PL.

The invention relates to a new simple cyclohexanehexol esters and herbicide compositions based on them.

Known to have a weed-killing action cyclohexandione General formula

< / BR>
where D is benzyl;

E - 2-ethylthiophen (U.S. patent 4440566);

D - benzyl, buta-2-enyl;

E - substituted five-membered heteroaryl radical (European patent application A 238021 and published European application A 125094);

D - benzyl, buta-2-enyl;

E - substituted phenyl (pronounced European application A 80301);

D - 2-thienyl, 3-Anil;

E - substituted phenyl (U.S. patent 4432786);

D - (E)-3-chlorpro-2-enyl;

E - methylthio-cycloprop-1-yl (European patent application A 243313).

Known to have a weed-killing action simple cyclohexanedione ester type compounds I, where E denotes a substituted 5-7-membered heterocycle; D is a substituted 4-phenyl-butylene radical or 4-fenilalaninemia (tiled application Germany A 3838309).

Object of the invention is the synthesis of these simple cyclohexaneacetic esters, which are compared with the known representatives of this class of compounds would be more selectivity in the fight against weeds in cereal crops such as rice and corn.

According to the invention have been found simple cyclohexanedione esters of the formula

< / BR>
where n = 0-2;

m is 0;

R1- C1-C6-alkyl;

R2- C1-C4-alkyl;

A - C1-C4-alkalinity or C3-C6-alkenylamine bridge, and each of these bridges may be substituted by 1 to 3 C1-C3-alkyl groups or possibly substituted by 1-3 C1-C3-alkyl groups Allenby bridge, containing in the chain 3-6 units, in which one SUB>-alkyl,

have a good herbicide action, preferably in relation to the species of the cereal family (Gramineen). They do not damage other plants and it may selectively be used in broad-leaved crops, as well as in the processing of monocotyledonous plants, not related to the family of grasses.

The invention relates to herbicide compositions. The composition includes an effective amount of the active ingredient is a simple cyclohexanoltramadol ether, which is used as compound of the formula I and the target additives.

Among the compounds according to the invention are characterized by selectivity in cereal crops and simultaneously suppress unwanted plants.

Simple cyclohexanedione esters of formula I can be obtained in various ways, in the first place preferably by well-known methods of the derivatives of formula II (European patent application A 243313) and related hydroxylamino formula III (European patent application A 169521) scheme

< / BR>
The reaction is preferably carried out in a heterogeneous phase in a solvent at a temperature below 80oC in the presence of a base, prse reaction grounds are, for example, carbonates, bicarbonates, acetates, alcoholate and oxides of alkaline or alkaline-earth metals, especially sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, and organic base is pyridine, and the tertiary amine is triethylamine. The basis of the type, for example, in amounts comprising from 0.5 to 2 mol.EQ. with respect to ammonium compound.

As suitable solvents, such as dimethylsulfoxide and alcohols, such as methanol, ethanol and isopropanol, aromatic hydrocarbons such as benzene and toluene, chlorinated hydrocarbons such as chloroform and 1,2-dichloroethane, aliphatic hydrocarbons such as hexane and cyclohexane, esters, such as ethyl ether, acetic acid, ethers, such as diethyl ether, dioxane and tetrahydrofuran. Preferably the reaction is carried out in methanol using sodium bicarbonate as the base.

The reaction is continued for several hours. The resulting product may be selected, for example, by concentrating the mixture, the distribution of the residue in methylene chloride/water and the removal of the solvent under reduced pressure.

For carrying out this method m is down. Depending on the type of solvent used for compounds II are given one - or two-phase reaction mixture.

Suitable for this variant solvents are, for example, alcohols such as methanol, ethanol, isopropanol and cyclohexanol, aliphatic and aromatic chlorinated hydrocarbons, such as hexane, cyclohexane, methylene chloride, toluene, and dichloroethane, esters, such as ethyl ether, acetic acid, NITRILES, such as acetonitrile and simple cyclic ethers such as dioxane and tetrahydrofuran.

Need to create special conditions for the reaction against a pressure not, therefore, work mainly at normal pressure.

Offer simple cyclohexanedione esters I have clearly acidic in nature, i.e. they can form salts with alkali or alkaline-earth metals, as well as complex enol ethers.

Alkali metal salts of compounds I can be obtained by treating 3-oxyconti hydroxide of sodium or potassium or a sodium alcoholate or potassium in aqueous solution or in an organic solvent, such as methanol, ethanol, acetone and toluene.

Other metal salts, such as salts mže with ammonia, hydroxide of phosphonium, sulfone or sulfoxide can be obtained ammonium salts and phosphonium.

To obtain hydroxylamine formula III are generally required to hold a number of known intermediate stages, the implementation of which originate from known intermediates. The process is carried out according to the scheme

< / BR>
where

L - tsepliaeva group, for example, halogen (chlorine, bromine, iodine), or CH3SO2-O-.

Necessary for synthesis of new hydroxylamino formula III alkylating agents can be obtained using known methods.

Optionally alkylating agents (5) can be obtained by known methods from carbinols (4).

Usually alkylating agent V or carbinol IV attached under option, Mitsunobu [1 Synthesis, 1981; Journ. Med. Chem. 33, 187 (1990)] to cyclic oxyimino VI and split the resulting protected hydroxylaminopurine VII to free hydroxylamine III, for example, using 2-aminoethanol.

In cyclic oxyimino VI D represents C2-C3-alkylene, C2-albaniles or containing up to three double bonds and, under certain conditions, one nitrogen atom a 5 - or 6-tier ring, such as phenylene, purdom VI is carried out in the presence of a base. Suitable for this purpose are the Foundation, with the ability to deprotonate oximity VI, not destroying emydoidea, i.e. the so-called dinucleophiles Foundation.

As examples of inorganic bases, such as carbonates of alkali and alkaline-earth metals, carbonates of alkali and alkaline-earth metals, organic bases such as aliphatic, cycloaliphatic and aromatic tertiary amines. Can also be used mixtures of these bases.

As specific compounds include, for example, the following grounds: carbonita sodium, potassium carbonate, magnesium carbonate, calcium carbonate, barium carbonate, hydrogen carbonates of these metals, trimethylamine, triethylamine, tributylamine, ethyldiethanolamine, N, N-dimethylaniline, 4-N,N-dimethylaminopyridine, diazabicyclo, diazabicyclo, N-methylpiperidine, 1,4-dimethylpiperazine, pyridine, quinoline, bipyridine, phenanthroline. It is preferable to use low-cost base, for example sodium carbonate or potassium.

The base is added in equivalent amounts or with an excess of about 5 EQ. in relation to oxyimino. More excess dopuskaet. It is preferable to use the base in the amount of 1-3, 1-2 more specifically EQ. in relation to oxyimino VI.

The use of nucleophilic bases, such as hydroxides of alkali and alkaline-earth metals, in particular sodium hydroxide and potassium hydroxide, are also possible. In this case, it is recommended to use the base in equivalent amounts with respect to oxyimino VI, in order to prevent nucleophilic effect of hydroxyl ion on the carbonyl function amidopropyl.

It is advisable to carry out the interaction of the parent compounds V with acetimidate VI in a solvent in which the reaction conditions remains inert. Preferred solvents are, for example, polemaeanus solvents, such as dimethylformamide, N-organic, dimethylsulfoxide, sulfolan and cyclic urea. The amount of solvent, as a rule, is not critical.

The interaction of the parent compounds V with acetimidate VI can also be carried out in conditions of interphase catalysis. In this case, use of a solvent which forms with water two phases, preferably chlorinated hydrocarbons. As phase transfer catalysts suitable ispolzuemaya ethers and crown ethers, [Dehmlow et al., Phase Transfer Catalysis. Verlag Chemie, Weinheim, 1980, p. 37-45, 86-93].

Interphase catalysts are used preferably in quantities of from 1 to about 10. %, especially from 3 to 5% vol. in relation to the volume of the reaction mixture.

The interaction of the parent compounds V with acetimidate VI carried out usually at a temperature of 0 - 140oC, preferably 2 - 100oC, namely 40 - 80oC. it is recommended that oxime VI were in the solvent together with the base, and the source connection V was added to this solution. Moreover, it is advisable to add oxime at low temperature, for example at 0 - 50oC, and only then heating the reaction mixture to the desired to the reaction temperature.

Upon completion of the reaction, the cooled reaction mixture is treated with water, and formed hydroxylaminopurine VII precipitate in the form of crystals or oil. Received hydroxylaminopurine may, if necessary, by recrystallization or extraction to purify further.

Hydroxylaminopurine VII can be identified as intermediates or directly to turn in hydroxylamine III (connection with the free AMI is described in lined with the application of Germany And 3615973, after using ethanolamine allocate hydroxylamine III. The selection of hydroxylamines III possible using other bases, such as aqueous inorganic bases, with amines, hydrazines, hydroxylamines or aqueous acids.

From the obtained reaction mixtures hydroxylaminopurine III can be isolated by usual methods, for example by extraction or crystallization. To increase the speed of crystallization of these hydroxylamines may be necessary to translate them using mineral acids or organic acids and their salts. For this purpose, as a rule, dilute solutions of these acids is subjected to interaction with hydroxylamine, preferably in approximately equivalent amounts. The salts of hydroxylamine as well as hydroxylamine III, with the free amino group can be directly processed in the herbicides of formula I or, if necessary, to put them in storage.

When receiving a simple cyclohexaneacetic esters of I the latter may represent a mixture of isomers, and is possible as a mixture of E/Z isomers and mixtures of enantiomers or diastereoisomers. The mixture of isomers in certain usl is I can be present in various tautomeric forms.

Taking into account the biological effectiveness of such preferred simple cyclohexanedione esters of the formula I where the substituents have the following meanings: n is 0, 1 or 2 when Z represents phenyl, and all X is halogen. If Z is a heterocycle, then the maximum possible value of n corresponds to the number of substituted ring links. If several radicals X substituents may be identical or different: m = 0; R1- C1-C6-alkyl, such as methyl, ethyl, propyl, n-butyl, especially ethyl and propyl; R2- C1-C4-alkyl, such as methyl, ethyl, propyl, n-butyl, especially methyl; A - C1-C4-alkylene, such as methylene, ethylene, propylene, butylene, propylen, prop-2-Anilin, butylen, but-2-Anilin, but-3-Anilin, penttinen, Penta-2-Anilin, Penta-3-Anilin, Penta-4-Anilin, hexarelin, Gex-2-Anilin, Gex-3-Anilin, Gex-4-Anilin, Gex-5-Anilin. They can be substituted by one to three methyl, respectively ethyl groups. When unsaturated chains can be either CIS-or TRANS-form. Preferred propylene, butylene, prop-2-Anilin, but-2-Anilin, but-3-Anilin;

or A - C3-C6-alkylene, in which a methylene group is replaced by oxygen atom, such as 3-oxopropyl, 3-oxabe. They can be substituted by 1-3 methyl or ethyl groups. Preferred 3-oxopropyl, 2-methyl-3-oxopropyl, 3-oxybutylene and 4-oxybutylene; Z represents phenyl; 5-membered heteroaryl-thienyl or isoxazolyl, preferably thienyl, X is halogen, such as fluorine, chlorine, bromine and iodine, especially fluorine and chlorine; C1-C4-alkyl, such as methyl, ethyl, n-propyl, 1-mediatile, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethylene, especially methyl and 1,1-dimethylethylene.

Example 1. 2-[1-[4-TRANS-(4-forfinal)but-3-relaxamento]propyl]-3-hydroxy-5- (1-methyltertiary)-2-cyclohexen-1-he (compound 1.1).

A mixture containing 2.0 g (7.8 mmol) of 3-hydroxy-5-(1-metaltitlepane)-2-propionyl 2-cylohexane-1-it, 1.6 g (9.0 mmol) of O-[4-TRANS-(4-forfinal)but-3-enyl]hydroxylamine and 100 ml of methanol, stirred for 24 h and then concentrated under reduced pressure. Output 100%.

1H-NMR (200 MHz, CDCl3): (1 hour to 1 million) of 0.77 (m, 2H); 0,97 (m, 2H); 1,10 (t, 3H) and 1.60 (m, 1H); to 2.13 (s, 3H); 2.40 a is 2.80 (m, 6H); 2,90 (q, 2H); to 4.17 (t, 2H); 6,10 (dt, 1H); to 6.43 (d, 1H); 7,00 (m, 2H); 7,30 (m, 2H); 14,80 (s, 1H).

Example 2. 2-[1-[4-TRANS-(4-chlorophenyl)but-3-relaxamento]propyl]-3-hydroxy-5- (1-methylthiazolidine)-2-cyclopenten-1-he (compound 1.3).

A mixture containing 2.0 g (7.9 mmol) 3-is silumina and 100 ml of methanol, stirred for 24 h and then concentrated under reduced pressure. Output 100%.

1H-NMR (200 MHz, CDCl3): (1 hour to 1 million) of 0.77 (m, 2H); 0,97 (m, 2H); 1,10 (t, 3H) and 1.60 (m, 1H); to 2.13 (s, 3H); 2.40 a is 2.80 (m, 6H); 2,90 (q, 2H); 4,20 (t, 2H); of 6.20 (dt, 1H); to 6.43 (d, 1H); 7,27 (s, 4H); 14,70 (s, 1H).

The most preferred simple cyclopentanedione esters of formula I are given in table. 1.

Simple cyclohexanedione esters I are suitable for use as herbicides, primarily to combat the plants belonging to the family Gramineen (cereals). In General, these esters have no harmful effects on the majority of plants and can be applied selectively in broadleaf crops, as well as for processing monocotyledonous plants, not related to cereals, primarily for processing corn and rice. However, some derivatives of the compounds I have a selective effect in relation to grass, so they can be used for targeted controlling undesirable plants.

Simple cyclohexanedione esters I and herbicide preparations containing these compounds, can be used, for example, in the form of solutions, designed specifically for spraying, powders, suspensions, the asty, preparations for pollination, soil, pellets, etc. Methods of their use can be very different; the spraying, splashing, soil, dusting, watering, and so on, i.e., depend on the purpose of the application. But in all cases should do its utmost to provide uniform and thorough distribution of the active substances according to the invention.

The compounds I are suitable for the preparation designed specifically for spraying of solutions, emulsions, pastes or oil dispersions. As inert additives can be used fractions containing mineral oils with a boiling range from medium to high, such as kerosene or diesel oil, oils from coal tar, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N,N-dimethylformamide, dimethylsulfoxide, N is an organic or water.

Water forms can be prepared from emulsion concentrates, zimulti, pastes or oil dispersions are themselves substances, either directly or after dilution in the oil or solvent, can be homogenized in water wetting agents, agents that increase the adhesion, dispersing agents or emulsifiers. Can be produced containing a wetting agent, a means of improving adhesion, dispersant or emulsifier and, under certain conditions, solvents or oil concentrates of the active substance with the ability to dissolve in water.

As surface-active substances can be used salts of alkaline and alkaline-earth metals, ammonium salts of aromatic sulfonic acids, such as ligninsulfonate, phenolsulfonate, naphthalenesulfonate and dibutylaminoethanol, as well as salts of fatty acids are presented, alkyl - and alkylarylsulfonates, alkyl-, laurilefirsulfat and sulfates of fatty alcohols, in addition, salts of sulfated hexa-, hepta - and octadecanol and simple glycol ethers of fatty alcohols, condensation products from sulphonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene, respectively naphthalenesulfonate with phenol and formaldehyde, simple polio utilityspecific ether, alkylarylsulfonate alcohols, isotridecyl alcohol, condensates of ethylene oxide of fatty alcohols, ethoxylated castor oil, easy polyoxyethyleneglycol ether or polyoxypropylene, acetate polyglycolide ester lauric alcohol, sorbitol complex ether, ligninolytic liquor or methylcellulose.

Powdered drugs, drugs for soil and dusting can be produced by mixing or joint grinding or grinding of active substances and particulate filler.

The granules such as pellets with sheath, impregnating and homogeneously pellets can be produced by binding of active ingredients and solid fillers. As solid fillers can be applied mineral lands, such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and products of vegetable origin, such as flour, cereals, flour from tree bark, wood flour, flour IO substances in the compositions is generally from 0.01 to 95 wt.%, preferably 0.5 to 90 wt.%. The degree of purity of the applied active substances is in the range from 90 to 100%, preferably 95 to 100% (according to NMR spectrum).

Example 1. A solution of compound 1.03 from 20 wt.h. in a mixture containing 80 wt.h. xylene, 10 wt.h. product accession, representing 8 to 10 mol of ethylene oxide on 1 mol of N-monoethanolamide butyric acid, 5 wt.h. salt calculatetype.recalculate, 5 wt.h. product accession, representing 40 mol of ethylene oxide on 1 mol of castor acid. Thanks to the careful distribution of the mixture in 100000 wt.h. water gain dispersion containing 0.02 wt.% the active substance.

Example 2. Dispersion connection from 1.05 to 20 wt.h. in a mixture containing 40 wt.h. cyclohexanone, 30 wt.h. Isobutanol, 20 wt.h. product accession, representing 70 mol ethylene oxide on 1 mol of isooctylphenol, and 10 wt.h. product accession, representing 40 mol of ethylene oxide on 1 mol of castor acid. A mixture of this dispersion with 100000 wt.h. soda contains 0.02 wt.% the active substance.

Example 3. Dispersion connection 1.07 20 wt.h. in a mixture containing 25 wt. hours of cyclohexanone, 65 wt.h. mineral oil fraction with temperature ceravolo oil. A mixture of this dispersion with 100000 wt.h. water contains 0.02 wt.% the active substance.

Example 4. Crushed in a hammer mill, a mixture of 20 wt.h. connection 1.09, 3 wt.h. sodium salt diisobutyrate--sulfonic acids, 17 wt. including sodium salt ligninsulfonate from sulfite liquor and 60 wt.h. powdered silica gel. Thanks to the careful distribution of the mixture in 20000 wt.h. water receive a liquid for spraying, containing 0.1 wt.% the active substance.

Example 5. Thoroughly mixed mixture of compounds 11.1 in the amount of 3 wt. hours and 97 wt.h. finely ground kaolin. This drug for dusting contains 3 wt.% the active substance.

Example 6. A stable oily dispersion connections 1.10 from 20 wt.h., 2 wt. including calcium salts of dodecylbenzenesulfonate, 8 mass.h. simple polyglycolic ether of fatty alcohol series, 2 wt.h. sodium salt mcevisualaid condensate phenolsulfonate and 68 wt.h. paraffin mineral oil.

Herbicide drugs, active substances, can be used for predsjedava or post-harvest processing. In those cases where the active ingredients are less compatible with certain kulturnymi sprayers is so, so drugs are not always impressed by the leaves of sensitive crops, as active ingredients get to the leaves growing among them undesirable plants or to free from vegetation plots soil.

The amount of applied active substance depending on the purpose of treatment, time of year, species of cultivated plants and the stage of their growth amount of 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (as.in.).

Given the diversity of processing methods, simple cyclohexanedione esters I and containing these substances drugs can be used in different cultures for controlling undesirable plants (table.4).

To broaden the spectrum of action and achieve sinergeticheskogo effect simple cyclohexanedione esters I can be used in a mixture with other groups of active substances with herbicide action and regulating the growth of plants. In this case, it is possible to conduct processing of crops by these mixtures. As ingredients for such mixtures can be used, for example, diazine, 4H-3,1-benzoxazinone, benzothiadiazine, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halogen-substituted carboxylic acid, troisville, having in the position 2, for example, carboxyl or carbamino group, derivatives of quinoline-carboxylic acid, imidazolinones, sulfonamides, sulfonylureas, aryloxy-, heteroarylenevinylenes acid, and their salts, esters and amides, etc.

In addition, it is advisable to apply the compounds I, without any additives or in combination with other herbicides in mixture with other crop protection agents, for example those which are intended for combating pests or phytopathogenic fungi and bacteria. The interest is also the use of compounds according to the invention in mixtures with solutions of mineral salts, which are used to compensate for nutritional deficiencies and necessary for the development of plants number of trace elements. You can use supplements revitalising oils and oil concentrates.

Herbicide simple cyclohexaneacetic esters of formula I was tested in experiments in the greenhouse.

As vessels for germination used plastic flower pots in which the substrate was a clay loam with humus content of 3.0%. The seeds of the experimental plants were sown separately.

For post-harvest processing of the experimental plants were grown in pot vessels or in advance, a few days before treatment, were transplanted in pots. Processing suspended or emulsified in water active ingredients is carried out depending on exteror only when the plants height from 3 to 15 see the number of active substances for post-harvest processing was taken from a calculation of 0.25 kg/ha

Taking into account the specific characteristics of plants kept at a temperature of 10-25oC, 20-35oC. the duration of the experiments was 2-4 weeks. During this time the plant was carried out proper care, observations and their reaction to certain kinds of processing. Evaluated the results, which used a scale graded from 0 to 100. 100 means that the shoots of plants otsutstvie the growth process.

In experiments in greenhouse used plant species that are listed in the table.5.

The results show that post-harvest processing of cereals held by the connection 1.05, gives a very good effect.

In particular, the connection 1.05 shows:

95% damage Echinochloa crus-galli, Setaria viridis and Setaria faberii at the rate of 0.25 kg/ha;

98% damage Echinochloa crus-galli at a flow rate of between 0.125 and 0.0625 kg/ha;

90% damage Digitaria sanguanalis at a flow rate from 0.125 kg/ha;

80% damage these plants with flow rates ranging from 0,0625 kg/ha.

While the harmful effects against rice at the expense of the substance in quantities of between 0.125 and 0.0625 kg/ha were observed.

Herbicide action connections 1.12 (A three-tier Allenova chain containing 1-methyl Deputy, where one link replaced by an oxygen atom; Z is phenyl; X is halogen) at the rate of 0.25 and 0.125 kg/ha (post-harvest application) against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Setaria faberii, and Setaria italica, is in each case 98, or 100%. Herbicide action connection 1.15 (A - methylene; Z - thienyl; X is halogen) at a flow rate of 0.25 and 0.125 kg/ha (post-harvest processing) against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, the CSO actions (post-harvest processing) obtained for compounds 1.17 (A - methylene; Z - isoxazolyl; X - methyl). The data are given in table.6.

Very good herbicide action show all of the compounds of formula I, including those in which A - methylsiloxane trinomial Allenova chain, one methylene link which is substituted by oxygen; Z - thienyl or isoxazolyl; X is halogen or methyl.

Data on herbicide activity of other compounds of formula I with the known compounds (EP-A368227) are given in table.7 and 8.

Herbicide activity of a compound 1.04 and compound A (1.9 from EP 368227) when used for post-harvest processing to 0.06 kg/ha of active substance in the greenhouse (table.7).

1.04

< / BR>
Connection comparison: R-C2H5SCH(CH3)CH2- (PL.7).

Herbicide activity of a compound 1.02 and connections compare B (1.11 from EP-A 368227) when applying for post-harvest processing to 0.06 kg/ha of active substance in the greenhouse (table.8).

1.02

< / BR>
Connection comparison B: R-C2H5-S-CH(CH3)-CH2(PL.8).

1. Simple cyclohexanedione esters of General formula I

< / BR>
in which n = 0 - 2;

m = 0;

R1- C1- C6-alkyl;

R2- C1- C4-alkyl;

A may be substituted by one or three C1- C3-alkyl groups, or not necessarily substituted with one to three C1- C3-alkyl groups Allenby bridge containing from 3 to 6 members in which one methylene group is replaced by oxygen atom;

Z - phenyl, isoxazolyl or thienyl;

X is halogen or C1- C4-alkyl.

2. Herbicide composition comprising an effective amount of the active ingredient is a simple cyclohexanoltramadol ether and the target additives, characterized in that as a simple cyclohexanoltramadol ether it contains a compound of the formula I on p. 1.

 

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m is 0, 1 or 2;

n 1-5;

q represents 0 or an integer from 1 to 5;

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The invention relates to the following compounds:

A) 4-(4-chloro-2-methylsulfonylbenzoyl)-5-cyclopropylmethoxy;

C) 5-cyclopropyl-4-(2-methylsulphonyl-4-trifloromethyl)- isoxazol; and

C) 4-(4-bromo-2-methylsulfonylbenzoyl)-5-cyclopropylmethoxy

The invention relates to chemical means of protection of plants, particularly to herbicide compositions and method of suppressing weeds with the use of the composition

The invention relates to derivatives of 5-aryl-isoxazol of, compositions containing them, methods for their preparation and their use as herbicides

The invention relates to synergistic combinations of the known fungicidal active ingredients and their use as plant protection

Herbicide tool // 2091022
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