Esters cyclohexanehexol and herbicide tool


(57) Abstract:

Usage: agriculture, chemical plant protection products, as substances with herbicide activity. The inventive product of General formula

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in which R1- a lower alkyl, A-CH2CH2-O-CH2CH2CH2-O-, -CH(CH3)CH2-O-CH2CH(CH3)-O-, Z is phenyl, X is halogen, n is 1, 2, 3, R2-2-ethylthiophen, 1-metaltitlepane, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl. Reagent I:

Reagent II: H2N-O-A-Z-Xn. Conditions of reactions: heterogeneous phase in a solvent with a boiling point below 80oin the presence of a base. Herbicide product contains the product in an effective amount and the target additives. 2 S. p. f-crystals,26 PL.

The invention relates to new herbicide-active esters cyclohexanehexol formula (I)

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in which R1lower alkyl group,

A CH2CH2O-CH2CH2CH2O-, -CH(CH3)CH2O - or-CH2CH(CH3)O-,

Z is phenyl,

X is halogen,

n 1, 2, 3,

R2-2-ethylthiophen, 1-metaltitlepane, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-the group of the General formula (I) have a pronounced acid character, that is, they can easily form the interaction products, such as salts of alkaline or alkaline-earth compounds or ethers of enols.

The compounds of formula (I) can exist in several tautomeric forms, each of which is included in the scope of claims of this invention.

In the literature described as herbicides esters cyclohexanehexol General formula (I)

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in which D is benzyl and E-2-ethylthiophen (U.S. patent 4,440,566),

D benzyl, and butenyl-2 and E substituted five-membered heteroaryl residue (European application 238,021, 125,094),

D benzyl, butenyl-2 and E-substituted phenyl (European application 80,301),

D butenyl-2 and E-5 to 7-membered heterocyclic ring containing up to two O, S atoms and two double bonds (EP-A 218, 233).

However, attempts have been made to find compounds that have high selectivity at low expenditure norms, that is amazing harmful plants without harming the cultural plants.

In accordance with this task were found new esters cyclohexanehexol formula (I), which differ a good weed-killing activity against undesirable grasses. Connections compatible with the x2">

Cyclohexanedione esters of the formula (I) can be obtained by known methods from known derivatives of the formula (II) (accepted European application 80, 301, 125, 094, 142, 741, American accepted claim 4, 249, 397, European accepted application 137, 174 and 177, 913) and related hydroxylamino formula (III) Houben-Weyl, 10/1, page 1181ff) (European accepted claim 169, 521) according to the scheme:

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It is advisable to carry out the interaction in the heterogeneous phase in a solvent with a boiling point below 80oC, in the presence of a base and apply hydroxylamine III in the form of its ammonium salt.

Suitable bases are, for example, carbonates, bicarbonates, acetates, alcoholate or oxides of alkali or alkaline-earth metals, in particular the hydroxides of sodium, potassium, magnesium, calcium. In addition, can be used organic bases as pyridine or tertiary amines. Base type, for example, in amounts of from 0.5 to 2 mol equivalents, counting on ammonium compound.

As a suitable solvent, such as dimethylsulfoxide, alcohols like methanol, ethanol and isopropanol; aromatic hydrocarbons as benzene and toluene; chlorinated hydrocarbons, as x ethers, as diethyl ether, dioxane and tetrahydrofuran. Preferably the interaction of methanol with sodium bicarbonate as the base.

The reaction ends in a few hours. The target compound can be selected, for example, by evaporation of the mixture, dissolving the residue in a mixture of methylene chloride with water and distillation of the solvent under reduced pressure.

But you can also for this interaction to directly apply the free base of hydroxylamine, for example, in the form of an aqueous solution; depending on the employed solvent for compound (II) receive one - or two-phase reaction system.

Suitable solvents in the case of this variant of the method are, for example, alcohols like methanol, ethanol, isopropanol and cyclohexanol; aliphatic and aromatic, in the case of chlorinated hydrocarbons as hexane, cyclohexane, methylene chloride, toluene, and dichloroethane; esters as ethyl acetate; NITRILES, as acetonitril; and cyclic ethers like dioxane and tetrahydrofuran.

Alkali metal salts of compounds of formula (I) can be obtained by treating 3-hydroxycodone sodium hydroxide or potassium hydroxide or alcoholate NAT is x2">

Other metal salts, as salts of manganese, copper, zinc, iron, calcium, magnesium and barium, can be obtained from the sodium salts of the known methods, as well as ammonium salts and phosphonium using ammonia, hydroxides of phosphonium, sulfone or sulfoxide.

Compounds of type (II) can be obtained, for example, from the corresponding cyclohexane-1,3-diones of the formula (IV) in which Y represents hydrogen or methoxycarbonyl known methods [Tetrahedron Lettr. 2491 (1975)]

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It is also possible for the compounds of formula (II) obtained according to the scheme through an intermediate stage of enol ethers, which in turn are obtained by the interaction of compounds of the formula (IV) with acid anhydrides in the presence of bases, and then immediately deposited defined production imidazole or pyridine (application for Japanese patent 79/063, 052).


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The compounds of formula (IV) can be obtained through a number of well-known stages of the method, proceeding from the known original products.

Synthesis of hydroxylamino formula (III) is carried out in accordance with the following reaction scheme: VII-III, where Y is a removable group, for example halogen such as chlorine, bromine, iodine or CH3SO2O-

Xn-Z-A-Y is Holocene known in the literature methods [see accepted application Germany 3,437,919, Tetrahedron Lettr. 28, 2639 (1970), Org. Synth. Coll. volume 1, 436 (1944); the joint patent application Germany 2,654, 646, 2,714,561, J. Org. Chem. 52, 3587 (1987); tiled patent application Germany 948,871, 948,872, J. Med. Chem. 26, 1570 (1983); Synthesis 675 (1983) and J. Org. Chem. 48, 4970 (1983).

Compound VII is treated with a cyclic hydroxyimino V and obtained a protected derivative of hydroxylamine VI decompose to free hydroxylamine III using, for example, 2-aminoethanol.

In cyclic hydroximino V D means, for example, C2-C3-alkylene, C2-C3-alkylene, C2-albaniles or 5 - or 6-membered ring containing up to three double bonds, and in the corresponding case 1 nitrogen atom, for example phenylene, peridinin, cyclopentyl, cyclohexyl or cyclohexenyl. As examples can be mentioned the following compounds

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The interaction of compounds of the formula (VII) with hydroxyamide formula (V) should be carried out in the presence of a base. Suitable are, in principle, every reason that can deprotonate hydroxyamide V without affecting kidney system. They, in particular, are the so-called dinucleophiles bases. As examples should be called, for example, mineral OS is, for example, mineral Foundation as carbonates of alkaline or alkaline-earth metals, carbonates of alkaline or alkaline-earth metals, carbonates of alkaline or alkaline-earth metals, organic bases as aliphatic, cycloaliphatic and aromatic tertiary amines. You can also use a mixture of these bases.

As individual compounds should include the following bases: sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, barium carbonate, bicarbonates of these metals, trimethylamine, triethylamine, tributylamine, ethyldiethanolamine, N,N-dimethylaniline, 4-N,N-dimethylaminopyridine, diazabicyclo, diazabicyclo, N-methylpiperidine, 1,4-dimethylpiperazine, pyridine, quinoline, bipyridine, phenantrene. Preferred are cheap Foundation of the carbonates of sodium and potassium.

The base type, as a rule, in equivalent quantities to excess 5 equivalents, counting on hydroxamic. Possible large excess, but it is excessive. The use of small amounts of base are also possible. However, the preferred number of grounds 1 to 3, in particular from 1 to 2 equivalents, counting on hydroxamic formula (V).

You can also use the sodium and potassium. In this case, it is advantageous to add a base in equivalent amounts with respect to hydroximino V to prevent nucleophilic attack carboxyl ions carbonyl function kidney group.

It is advisable to carry out the interaction, the source compounds of the formula (VII) with hydroxyamide V in a solvent inert to the components of the reaction conditions. Preferred solvents are, for example, polar aprotic solvents, such as dimethylformamide, N-organic, dimethylsulfoxide, sulfolan and cyclic urea. The amount of solvent, as a rule, are not critical.

The interaction of the parent compounds VII with hydroxyamide V can be carried out also in the application of catalysis in conditions of phase transfer. In this case, use of a solvent which forms with water two phases, preferably chlorohydrocarbons. As catalysts phase transfer suitable usually used for such purposes Quaternary ammonium salts and Weinheim, 1980. The transfer catalysts should be used in quantities of from 1 to about 10. preferably in quantities of from 3 to about 5. counting on the volume of the reaction mixture.

Interaction>, particularly preferably from 20 to 100oC, and, in particular, from 40 to 80oC. it is Expedient to do so, to hydroxamic V instead of the base were in the solvent and the source connection of the formula (VII) was added to this solution. When this proved successful, with the addition of hydroxyamide at a lower temperature, for example at 0, 50oC, and only then heating the reaction mixture to the desired reaction temperature.

Upon completion of the reaction, the cooled reaction mixture, it is advisable to dilute it with water, with the resulting hydroxylamine derivative VI are deposited in the form of a crystalline solid or in the form of oil. Thus obtained derivative of hydroxylamine, you can optionally clean or crystallization or extraction.

Derivatives of hydroxylamine VI can be subjected immediately becoming a hydroxylamine derivative III with a free amino group. This transformation can be performed by known methods described, for example, accepted the proposal of Germany 36, 15, 973 and cited in her publications. It is preferable to carry out the method in relation to the accepted application Germany 36, 15, 973, in which the hydroxylamine derivative is of Sevani, as aqueous mineral bases, amines, hydrazines, hydroxylamine or with aqueous acid.

From the reaction mixtures obtained in this way, it is possible to allocate derivatives hydroxylamines III using conventional methods of isolation, for example, by extraction or crystallization. To increase the tendency to crystallization of these derivatives hydroxylamino it is often necessary to translate them into a salt with mineral or organic acids. For this purpose, as a rule, dilute solutions of these acids are interacting with their salts with mineral or organic acids. For this purpose, as a rule, dilute solutions of these acids are subjected to interaction with derivatives hydroxylamino, it is advisable in equivalent quantities. The salts of hydroxylamine can be processed further as a derivative of hydroxylamine with free amino groups directly to herbicides of the formula (I) or, if necessary, to keep them that way.

From the point of view of biological activity cyclohexanedione esters of the formula (I) are preferred with the following value deputies;

R1-alkyl, like methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2.2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpropyl, 2-methylpentyl, 2-methylpentyl, 4-methylpentyl 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,2-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, in particular ethyl and propyl.

A-C3-alkylene, in which a methylene group is replaced by oxygen atom, such as 3-oxypropylene. The most preferred 2-oxypropylene.

Esters cyclohexanehexol formula (I) are suitable as herbicides, in particular for combating plant from the family of grasses.

The subject invention is also herbicide agent, comprising the active ingredient esters cyclohexanehexol formula (I), in an effective amount and the target additives.

Esters cyclohexanediol formula (I) or containing these substances herbicide tools can be applied, for example, in the form directly to the spray solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil suspensions, pastes, powders for spraying, drugs for soil in the form of granules or their selected depending on the purpose, each method should ensure the most subtle distribution of the effective substances in accordance with the invention.

The compounds of formula (I) are suitable, as a rule, for the preparation directly to the spray solutions, emulsions, pastes or oil suspensions. As inert additives should be borne in mind fractions of mineral oils with medium to high boiling points such as kerosene or diesel oil, furthermore, oils of natural origin, as vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons, such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanone, cyclohexanol, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethylsulfoxide, N is an organic or water.

Applied aquatic forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or dispergiruyushchie in water granules by adding water. To obtain emulsions, pastes or oil dispersions can substances, as such or dissolved in an oil or solvent, homogenize is part of concentrates, consisting of a biologically active substance, wetting, grasping, dispersing or emulsifying substances, and also solvents or oils, which are suitable for dilution with water.

As surface-active substances should be kept in mind salts of alkaline, alkaline-earth metals, ammonium, aromatic sulfonic acids, for example lignin-, phenol-, naphthalene - and dibutylaminoethanol, as well as fatty acids, alkyl - or alkalicarbonate, alkalemia or lauric esters of sulfates of fatty alcohols, and salts of sulfated hexa-, hepta - and oxododecanoyl, as well as glycol ethers of fatty alcohols, condensation products from sulphonated naphthalene and its derivatives, obtained with formaldehyde, condensation products of naphthalene or naphthalenesulfonate with phenol and formaldehyde, polyoxyethylenesorbitan esters, the ethoxylated isooctyl, octyl or nonylphenols, polyglycidyl ether of alkylphenol, tributyltinchloride ether, alcohols of alkylarylsulfonate, isotridecyl alcohol, condensates of ethylene oxide and fatty alcohols, ethoxylated castor oil, polyoxyethylenesorbitan esters or polyoxypropylene, acetate polypi Means in the form of granules, powders for soil and powders for spraying can be prepared by mixing or fine grinding of biologically active substances with solid carriers.

Granulates, for example, with sheath, saturated and homogeneous, can be prepared by linking biologically active substances with a solid carrier. Solid carriers are mineral, as silicic acid, silica gel, silicates, talc, kaolin, unslaked lime, chalk, bolus, clay, dolomite, hard-shelled earth, calcium sulfate and magnesium, magnesium oxide, powdered polymeric substances, fertilizers as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products, such as flour, cereals, flour of wood chips, walnut shell, powdered cellulose or other solid carriers.

Preparations contain as a rule, from 0.02 to 95 weight. preferably from 0.5 to 90 weight. biologically active substances. The active substance used with a purity of from 90 to 100%, preferably 95-100% (GC/jhud or NMR-spectra).

Herbicide means in accordance with the invention can be prepared, for example, as follows:

1.Mix 90 weight.h connection N the fir.

2. 20 weight. including connection N7.23 dissolved in a mixture containing 80 weight.h xylene, 10 weight.h condensation products of 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanolamide butyric acid, 5 weight.h the calcium salt of dodecylbenzenesulfonate and 5 weight.h. the condensation product of 40 mol of ethylene oxide with 1 mol of castor oil. In the draining and delicate mixing of the solution with 100000 weight. including water receive water dispersion, which contains 0.02 weight. biologically active substances.

3. 10 weight.h. connection N7.21 is dissolved in a mixture of 40 weight.h. cyclohexanone, 30 weight. h Isobutanol, 20 weight. including condensation products of, 7 mol. of ethylene oxide and 1 mol of isooctylphenol and 10 weight. including condensation product of 40 mol of ethylene oxide and 1 mole castor oil. By prilipanie and subtle stirring of the solution in 100000 weight. including water receive water solution (dispersion), which contains 0.02 weight. biologically active substances.

4. 20 weight. including active substances N7.23 dissolved in a mixture consisting of 25 weight. hours of cyclohexanone, 65 weight. including fractions of mineral oils with a boiling point from 210 to 280oC and 10 weight. including condensation product of 40 mol of ethylene oxide and 1 mol of castor oil. By contributing and subtle mixing receive a solution to 100000 . 0 weight. including active substances N7.23 well mixed with 3 weight. including sodium salt diisobutyrate- --sulfonic acids, 17 weight.h. sodium salt ligninsulfonate obtained from sulfite lye, and 60 weight.h powdery silicic acid gel, and pulverized in an impact mill. In the fine grinding the mixture in 20,000 weight.h.water get the solution for spray, which contains 0.1 weight. biologically active substances.

6. 3 weight.h. the active substance N7.15 mixed with 97 weight. including finely ground kaolin and thus get the powder for spraying, which contains 3 weight. the active substance.

7. 30 weight. including active substances N7.21 subtly mixed with a mixture consisting of 92 weight. hours of powdered silica gel and 8 weight. including paraffin oil, which POPs on the surface of the silicic acid gel. So get ready preparation of biologically active substances with good tack.

8. 2 weight. including active substances N7.23 subtly mixed with 2 weight. including the calcium salt of dodecylbenzenesulfonate, 8 weight. including polyglycolic ether fatty alcohol, 2 wt. including sodium salt of a condensate of phenol-urea-formaldehyde and 68 weight. including parafirovanija shoots. If the active substance is not very compatible with some cultivated plants, that use such methods of application, in which herbicide tools are applied to plants with special devices for applying to the leaves of protected plants as possible to touch, while the active substance must fall on the leaves and the surrounding land undesirable plants

Expenditure norms active substances are depending on the time of year, the green of plants and the growth stage, from 0.001 to 3 kg/ha, preferably 0.01 to 2.0 kg/ha.

Covered action spectrum for weed control, compatible with cultivated plants or the desired impact on the growth of these plants, as well as the variety of application methods all make connections in accordance with the invention with a large number of cultivated plants,to the following:

To broaden the spectrum of action and to achieve synergistic derivatives cyclohexenones formula (I) can be mixed both with one another and with representatives of other herbicide or regulating the growth of plants groups of biologically active substances and apply yourself. Examples of possible components of the mixtures are diazine, 4H-3,1 Ben the new acid, triazine, amides, urea, diphenyl ethers, triazinones, orally, derivatives benzofuran, quinoline-carboxylic acid derivatives of the sulfonylureas, cyclohexanone, hetero-aryloxypropanolamine acid, and their salts, esters, amides, etc.

In addition, it is useful to use derivative cyclohexanedione esters of the formula (I) or herbicide products containing them alone or in combination with other herbicides or other pesticides and apply, for example, with means for combating pests or phytopathogenic fungi or bacteria. Of interest, also mixed with solutions of mineral salts, which are used to increase the content of nutrients and trace elements. You can also add neotomine oils and oil concentrates.

In the following examples of synthesis used the corresponding starting compound for other hydroxylamino formula (III) and cyclohexanedione esters of the formula (I); the compounds described in the table below with the physico-chemical data.

Examples of obtaining hydroxylamines III.


To pyrrolidone After 5 h at 60oC cold reaction mixture is poured into 2000 ml of ice water, the precipitate is sucked off, washed with water and isopropanol and dried in vacuum over phosphorous pentoxide 185 g (82%) phthalimido ether. So pl. 62 64oC; NMR Spectrum-1H (250 MHz, d6-DMSO): 3,85 (m, 2H); of 4.35 (m, 2H)+ 7,10 7,40 (m, 4H); 7,88 (s, 4H).


184 g (of 0.58 mol, obtained as described above) ether phthalimide portions contribute in 270 ml of ethanolamine. After 3 h at 60oC cold reaction mixture is poured into 1000 ml of ice water. The hydrolysate extracted three times with dichloromethane portions 800 ml the combined organic phases are washed with 200 ml saturated sodium chloride solution, dried over magnesium sulfate and evaporated in vacuum. Get 98 g (91%) hydroxylamine.

1H-NMR spectrum (250 MHz, CDCl3):d 3,70 (dd, 2H); of 3.85 (dd, 2H); of 4.54 (s, 2H); 5,50 (br.s. 2H); 7,00 7,50(m, 4H).

An example of retrieving ether cyclohexasiloxane I

2-[1-[[2 -(2-forbindelse)ethoxy]imino]butyl] -3 - hydroxy-5-(2H-tetrahydropyran-4-yl) -2 - cyclohexen-1-it.

A mixture of 4.0 g (10 mmol) 2-butyryl-3-hydroxy-5- (2H-tetrahydropyran-4-yl)-2-cyclohexen-1-she and 2.6 g (14 mmol) of O-[2-(2 - forbindelse)ethyl] -hydroxylamine in 100 ml of methanol is stirred for 24 hours Reakciyu liquid: ether). Get 3.5 g (54%) ether cyclohexasiloxane.

1H-NMR (300 MHz, CDCl39:d of 0.93 (t, 3H); 1,20 to 1.77 (m, 7H); 1,90 (m, 1H); of 2.23 (m, 4H); of 2.58 (m,2H); 2,92 (m2H); to 3.38 (t, 2H); of 3.80 (m, 2H); is 4.03 (m, 2H); 4.25 in (m, 2H; and 4.68 (s, 2H); 6,93 is 7.50 (m, 4H); 14,30 (s, 1H).

The results of the tests are presented in table.1-14.

Examples for the application.

Herbicide action esters cyclohexanehexol formula (I) shown by experiments conducted in the greenhouse.

As vessels for the cultures served plastic flower pots with clay sand with approximately 3% of the manure as substrate. Seeds of the test plants separately.

When processing before germination dispersed or suspended in water biologically active substance was applied directly after sowing by means of finely spray nozzle. The vessels were slightly damp, to ensure germination and growth, and directly after that were covered with permeable plastic cylinders to the germination of plants. These coatings contributed to the uniform germination of the tested plants, because they had not been harmed by biologically active substances.

Order processing after germination seedling AI dispergirovannykh in the water with biologically active substances. Expenditure norms for a method of processing after emergence of seedlings was 0.25 kg/ha.

Plants withstood depending on their type when 10 25oC or 20 - 35oC. Experience continued for 2 to 4 weeks. At this time the plants are cared for and assessed their response to individual processing.

The evaluation was performed on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least part of the above ground, and 0 is no damage or normal growth process.

For testing in the experiments were taken from the following types of greenhouse plants: the results of the analysis of Italian, 3; green spickle.

In the experience when processing after emergence of seedlings used 0.25 kg/ha, the active compounds of example 7.21 and 7.23, if this had been a very good defeat unwanted herbaceous plants with simultaneous compatibility with the culture of rice. All the compounds of formula (I) show similar activity against rice.

To confirm herbicides actions declared esters cyclohexanehexol formula (I) were tested to failure of the weeds listed herbicide-active compounds. For IP is found beginning in 1 l of a mixture of 93 weight. xylene and 7 weight. lutensolRAP8 (wetting agent with emulsifying and dispersing action based on the eight of ethoxylated Nonylphenol).

The results of the tests are presented in table. 15 -19

Polyfunctional compound N3.29 formula

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is a highly radioactive substance. Thus, when the amount of consumption of this compound is 0.05 kg/ha (treatment after germination) achieved 100% action against undesirable plants Echinochloa cruss galli (barnyard grass) Lolium-Polygonum.

The following experiments were carried out in accordance with S. 65 description. In this connection N2.39 was subjected to comparison with the known from EP-A 218, 333 comparative products A-D, the formulas of which are set out in table.20:

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From the data the following tables 21 and 22 it is clear that the compounds according to the invention show a better effect. In addition to a good herbicide action comparison examples A and C shows very good selectivity in the culture of rice. Damage in the amount of 55 and 65%, respectively, which can be seen when using A and C, respectively, are not valid when used in this culture. Compared with the compounds B and D connection according to the invention exhibits a higher herbicide AK is inane according to the invention is confirmed by the examples, listed in table.24 and 25. The product is obtained as an emulsion concentrate in a mixture of 7% Luthensol AP8 (alkylphenolethoxylates) and 93% of xylene, and the content of the active substance is 100 g/L.

Below is additional evidence of a positive effect for compounds N 12.01, 12.02, 13.01 and 13.02. The experiments were conducted by the methods described on pages 65 and active substances were applied after emergence (the consumption rate of 0.25 kg/ha of active substance). The spray solution contained 100 g of the active substance in 1 liter of a mixture comprising, by weight, 93. xylene and 7 wt. LutensolAP8.

Table 26 contains the results obtained in the greenhouse. From these results it follows that the tested compounds have a high degree of selectivity in relation to winter wheat.

1. Esters cyclohexanehexol General formula I

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where R1lower alkyl group;

A-CH2CH2O, CH2CH2CH2-O-, - CH(CH3)CH2-0 -, or-CH2CH(CH3)-0-;

Z is phenyl;

X is halogen;

n 1, 2, 3;

R22-ethylthiophen, 1-metaltitlepane, tetrahydro-Piran-3-yl, tetrahydropyran-4-yl, tetrahydrate-Piran-3-yl.

2. Herbicide agent, vlocalclientname it contains a compound of General formula I according to p. 1 in an effective amount.

Priority points:

09.05.90 on PP. 1 and 2;

20.10.90 on PP. 1 and 2.


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