CS221280B2 - Herbicide means and method of making the active substances - Google Patents

Abstract

1. Ureas, with cyclic substituents, of the following general formula I see diagramm : EP0028829,P26,F1 in which A = see diagramm : EP0028829,P26,F2 including the positional isomers, in particular the transform with Rx denoting OH or carboxyl ; Ry denoting H or acyl ; R denoting hydrogen, hydroxyl, alkyloxy or acyl, a C1 -C12 -alkyl radical, optionally with hydroxyl groups, which can be straight-chain or branched and interrupted by oxygen and/or nitrogen atoms, a C3 -C13 -cycloalkyl radical, optionally with alkyl substituents, which can be interrupted by oxygen and/or nitrogen atoms, and/or with hydroxyl groups and/or with an aliphatic or aromatic acyl group and/or with carboxyl or carboalkoxy groups, a C2 -C5 -alkenyl or alkenyl radical, or a phenyl radical which can be substituted by alkyl and/or acyl and/or hydroxyl and/or dialkylamino groups ; R**1 denotes hydrogen or a straight-chain or branched C1 -C4 -alkyl radical or alkoxy radical ; R**2 denotes hydrogen or a straight-chain or branched C1 -C4 -alkyl radical, optionally with hydroxyl groups, or C1 -C4 -acyl radical and gamma denotes a number from 0 to 1.

Description

In ^yn Alez relates herhchního ^p rost ^of the composition, contains ^the esters of I ^to a composition effective ^to novel ureas ^d Eriva ^y with ^y ^ cyclohexylalanyl YMI substitoent ^y. · Furthermore ^the invention th e from ^{p to} s u ^b uso productions ^b y the n ch ^AC herbicidally ^No innýc ^h ^ DENV Tů ureas with cyclic substituents.

The prior art already known cykloalkylděriváty urea and thiourea ^b ECN it ^é formula

the ring containing 5-8 carbon atoms, ^{in some} M ^F

R, R ^1, R ² him / and R ³ represent ^s hydrogen ^{to b} not on alkyl, or

R ¹ R ² and / or R @ ^{3 I} C ^{YKL plurality of projections} nominal cycloalkyl group, · or alkenyl or aryl and

X means oxygen or sulfur; and

^R2 and R3 may also be part of a common ring, and. as compounds with herbicidal activity.

NAME ^OF · ^Ké are the urea derivatives of ^dp ovídající structures which may contain on the cyclohexyl ring to · three methyl groups, which are not mutually adjacent positions.

The^to is, for example, urea sputum^bwell known process from dimethylcyclohexylamines (2,6-, 2,4-, 3,5-, 2,5-^dirneth^ylc^yklohex^ylamin^at) in U.S. Pat^pisu 3 3⁴⁷ 6⁵8. Pro ·^pr^pravu N^,N ‘· symmetrically aliphatic, residues of disubstituted allophanyl chlorides that provide thermal decomposition^kland^dfor cleavage of hydrogen chloride^pŘslušné^andSat^toyanates^, se^pou^žíva ^ №-б1 (2,4,64гппеhylcy ^ ohexy ^ urea)^toé pa No. 3 275 669 and 3 337 621).

AT^Cin^ky from above^dených c^ykloal^kyureas are all^to I^to in^eventad^{ě p}use of total herticides^ki if used both^O games^biC^idů aphhovaných preemer^Gent ^ ě^, as well^and for d^hiveE^{žité k}at^lturni plants ta^ké at^afterst emergent application, still unsatisfactory in appearance^to tom ^^ofand their herbicidal. efekt^ek je p^say low^toand against certain · very^roof^šsmoked grass^pleve^lům inadequately sociable because s^ytheir phytotoxicity increases rapidly with higher application rates.

According to U.S. Pat.

671,637 and 3,686,303 disclose compounds of the general formula

which are suitable as repellents.

Surprisingly, it has now been found that certain hitherto unknown three or more times substituted cycloalkyl ureas, in particular those which also contain geminal substituents on the cycloalkyl radical, as well as ring-substituted ureas which are substituted as described above, exhibit in comparison with known comparable derivatives urea significantly improved chamomile effect.

The subject of the present invention is a berbicidal composition, characterized in that it contains at least one compound of the formula I as active ingredient.

R2

OF

R — NR1 — C — N (Г),

X R3 wherein

R is a group

H _b c CH ₃

X is oxygen or sulfur; and

R1 is hydrogen or methyl,

R 2 and R 3 are the same or different from each other and represent hydrogen, methyl, a group, a methoxy group or a phenyl group.

Among the novel compounds of formula (I), those in which R 1, R ² and R 3 are one hydrogen are preferred, and the remainder are as defined above.

The novel cyclic urea and thiourea derivatives of the aforementioned general formula I have significantly better herbicidal properties than the urea derivatives used hitherto. Especially when pre-emergence or post-emergence treatments are carried out, these compounds have an excellent effect on the weed control and are not phytotoxic to crop plants.

The invention therefore also relates to the use of urea derivatives with cyclic substituents of the formula I as herbicides.

The compounds of formula I are prepared according to the invention by reacting the compounds of formula I

R - A with compounds of formula

R2 \ N-B,

R3 wherein

A is NCO or NOS; and

B is hydrogen, or

A is -NR 1 and

B is COC1 or CSC1, and

R, R 1, R 2 and R 3 are as defined in formula I.

The preparation of the novel compounds of formula I can be illustrated, for example, by:

1a] by reacting compounds of formula III with compounds of formula II:

R2 R1R2

R — NCX 4- HN --- R — N — C — N

X, 1 X, X R3 (II) (III ·) (AND) whereas

R, X, R 2 and R 3 have the meanings given in formula I, the radical R does not contain a hydroxyl group, and

R 1 is always hydrogen, or

R2 / 1b) by reacting compounds of formula IV with compounds of formula V

RiRi

I, I

R1-NH + XCN-R2-> R-N-C

X H (IV) (V) (I ‘) wherein, in these formulas, R 1, X and R 2 and R 1 have the meanings given under formula I (R 3 is thus always hydrogen in these reactions).

The starting materials of the formulas II to V are only partly known from the literature and, if appropriate, can be prepared by methods known per se.

The reaction leading to the new ureas of formula I is carried out in inert solvents such as acetone, ether, dioxane, gasoline, benzene, toluene, xylene and chlorinated aliphatic or aromatic hydrocarbons, at temperatures from 0 ° C to the boiling point of the reaction. mixtures, preferably at temperatures between 20 and 160 degrees Celsius, optionally with the addition of tertiary alkylamines or metal salts, such as preferably dibutyltin dilaurate (DBTL), aluminum- or zinc-alkyl / alkoxy or / and -halo derivatives.

If a reactant of formula (III) or (IV) containing a hydroxyl group or a hydroxyl-containing group is used for this reaction, the isocyanate dissolved in an inert solvent is preferably added dropwise with stirring, for example to:

The novel compounds of formula (I) are further obtained, for example

2a) reaction of carbamoyl chlorides of formula VI with primary or secondary amines of formula VII in equivalent amounts or in excess under basic conditions:

R ¹ R | /base

R —N —C —Cl + NH>

II \

XR3 (VI)

R ¹ R 2

AND/

----> R — N — C — N + HCl

II \

X R3 (I) or

2b) reaction of carbamoyl chlorides of formula VIII with primary or secondary amines of formula IX in equivalent amounts or in excess under basic conditions:

In the process according to process 2b], R, R ¹ , R ² and R ^{3 are} as defined in formula I, but neither R ² nor R ³ can be hydrogen.

The starting materials of the formulas (VI) to (IX) are partly known from the literature or are prepared by methods known per se. Their reaction, which leads to the new ureas corresponding to formula I, is carried out in inert solvents such as ketones, ether, dioxane, gasoline, benzene, toluene, xylene and chlorinated aliphatic or aromatic hydrocarbons at temperatures up to 0 ° C up to boiling point. of the reaction mixture, preferably at temperatures between 70 ° C and 220 ° C in the presence of hydrogen chloride-binding bases, for example tertiary amines such as pyridine or triethylamine or potassium carbonate in anhydrous medium. After completion of the reaction, the resulting salt is washed with water, then again with an aqueous alkaline solution until neutral, the solution is dried and concentrated, often resulting in the formation of urea in solid crystals.

Special representatives of the compounds thus obtained can be converted into other compounds of formula I by other known reactions, for example by saponification, salt formation, esterification, re-esterification, alkylation, alkylation or alkoxylation, but in most cases it is easier to prepare the reactants necessary for urea formation (b) and (2a) and (b), so as to correspond in structure to the desired compound of formula (I).

Typical examples of compounds of the invention which correspond to formula I are given in Table 1 below:

Table 1 example number formula

R ² R 1 is a base

N — C — C14-HN — R ---- μ. (I) / II

R ³ O (IX) (IX)

In the process according to process 2a), R, R ¹ , X, R ² and R ^{3 are} as defined in formula I, but R ¹ must not be hydrogen and R must not contain a hydroxyl group.

formula number example

NH-C-NH-CH

II ³

WITH

In the following, the invention is illustrated in greater detail by the examples representative of the preparation of the compounds of the above general formula (I).

Example 1

N- (3,3,5-trimethylcyclohexyl) Urea

Dissolve 0,5 mol of 3,3,5-trimethylcyclohexylamine in 240 ml of glacial acetic acid and 100 ml of water at 40 ° C. To this solution is added a solution of 1 mol of sodium cyanate in 100 ml of water at 40 ° C. About 1/10 of this solution is added dropwise with stirring slowly until a white crystalline precipitate is formed, and the residue is then added very rapidly with vigorous stirring. The reaction temperature rises to about 55 ° C. The resulting slurry was stirred for Ϋ4 hours and then allowed to stand at room temperature for 2 to 3 hours, diluted with water, cooled to 0 ° C, filtered, washed with water and dried.

Yield: 84.5 g of white crystalline powder (92% of theory).

Recrystallization from aqueous acetone gave a very pure product.

Analysis:

calculated:

C: 65.23%, H: 10.86%, N: 15.2%;

C: 65.3%, H: 10.7%, N: 15.2%.

. Melting point: 182-184 ° C.

Example 2

N- (3,3,5-trimethylcyclohexyl) -N‘, N‘-dimethylurea

CH ₃

NH-C-N 11 o

0.25 mol 41,7 g of 3,3,5-trimethylcyclohexyl isocyanate are dissolved in 50 ml of benzene and this solution is added to a solution of 0,25 mol

10.2 g of dimethylamine in 100 ml of benzene with vigorous stirring. The reaction mixture was then heated under reflux for 1 hour. After cooling, the reaction solution was washed with 2N aqueous hydrochloric acid, 2N aqueous sodium hydroxide solution and water, respectively, and the organic phase was dried over sodium sulfate. By evaporating the solvent, the solution is concentrated to obtain crystals which are recrystallized from n-hexane to give the title urea as crystals.

Yield: 51.2 g (98.7% of theory).

Analysis:

calculated:

C: 67.94%, H: 11.31%, N: 13.21%;

П д] р ΤΟΤΊ η ·

С: 67.4%, Η: 11.5%, Ν: 13.4%.

Melting point: 85-87 ° C.

Example 3

N- (3,3,5-trimethylcyclohexyl) -N‘-methoxyurea

A solution of 0.25 mol and 8.3 g of hydroxylamine in 50 ml of benzene is added to a solution of 0.25 mol A and 41.7 g of 3,3,5-trimethylcyclohexyl isocyanate in 50 ml of benzene. The mixture was stirred well and allowed to stand overnight. The precipitated crystals are filtered off and washed with n-hexane to obtain N-3,3,5-trimethylcyclohetyl) -thyroxyurea.

Yield: 49.6 g (99.2% of theory).

To 0.2 mol and 40 g of this urea derivative is added a solution of 54 g of sodium methoxide in 100 ml of methanol. The mixture is homogenized by stirring and 0.2 mol. The solvent was evaporated and the residue was extracted with benzene after addition of water. The benzene solution was dried over sodium sulfate and concentrated to give crystals. The crystals obtained are recrystallized from a mixture of n-hexane and benzene, whereupon. to give the title compound.

Yield: 41.8 g (97.6% of theory).

Analysis: calculated:

C: 61.69%, H: 10.27%, N: 13.08%;

finds no:

C: 62.0, H: 9.9%, N: 13.08%.

Melting point: 114-117 ° C.

Example 4

N- (3,3,5-trimethylcyclohexyl) -N-methyltN, N‘dimethylurea

To a solution of 0.5 mol and 77.6 g of N-methyl-3,3,5-trimethylcyclohexylamine in 100 ml of benzene is added a solution of 0.25 mol and 26.9 g of Ν, Ν-dimethylcarbamoyl chloride dissolved in 100 ml of benzene. The temperature of the mixture exits from room temperature to 80 ° C in the reaction and is maintained at 80 ° C for 1 hour. The amine hydrochloride is then shaken with water, the benzene solution is separated, dried with sodium sulphate and concentrated. A white crystalline precipitate formed from the concentrated solution.

Yield of the title compound: 53.6 g (94.8% of theory).

Analysis:

calculated:

C: 69.04 Oo, H: 11.5 Oo, N: 12.39%; found:

C: · 69.4 · Oo, H: 11.2%, · N: 12.2% .::

Melting point: 79-82 ° C.

To the aqueous phase in which the amine hydrochloride is dissolved, an equivalent amount of aqueous sodium hydroxide solution is added to obtain the amine, and the liberated amine is extracted several times with benzene. After traction distillation, the amine used for acid binding is recovered in almost quantitative yield.

Example 5

N- (2,4-Methoxyphenyl) -N‘-phenylthiourea

A solution of 0.2 mol й 25.4 g of cyclopentylamine in ⁵⁰ mL x ^y ene was added to a solution of 0.2 mole of $ 27 g phenyl isothiocyanate ⁱⁿ 50 mL x ^y Lena and ^PI ECE S ^ chtte dibutyltin dilaurate was added. as a catalyst. The mixture was allowed to reflux for 6 hours. The reaction solution was washed with 2N aqueous hydrochloric acid, 2N aqueous sodium hydroxide solution and water, respectively, and the organic phase was dried over sodium sulfate. Subsequent evaporation of the solvent gave a crystalline precipitate from the concentrated solution, which was filtered off and recrystallized from a mixture of benzene and n-hexane.

Yield ^of obstructions: ^{49.4 g (4.2} 9% of theory).

Analysis:

calculated:

C: 68.69%, H ^: 8.39 0/0, N: 10.68 o / _o ,

S: 12.24%;

^C: 6 ⁹ 01 ^{H: 8,} 7% · N: ¹⁰ 3%

^{S: 12,} 1%.

M.p .: 149-153 ° C.

Example 6

N- (1,3,3-Trimethyl-5-hydroxy-cyclohexyl) -methyl-N, N, N-dimethylthiomethyl

CH ₄ ³

--- л

К mites ^{to 0.5} mole with ^{85.5 g} · ¹ · -aminometh ^{yl t3-hydroxy-5,5} -triene ^{and meth yl cyclo-} lohexanu in ¹⁵⁰ ml ^of toluene is added dropwise a solution of 0.25 mol · 30.9 g of N, N-dimeth-4-thiocartic acid chloride in 100 ml of toluene, the reaction temperature rising to 80 ° C. The reaction is allowed to reflux ^1Х / г ^h o ^{d y} in. The amine used in creating excessive TKU ^s to scavenge the acid to form the hydrochloride, extracted with water and separately recovered, the organic phase is dried and concentrated until crystallisation of the title urea derivative.

^In ýtě ^from EC: ^{62.1 g} (96.2% of theory).

Analysis:

calculated:

^C: 60.46%, ^{H: 10,} 07 <10% ^N, 85% S 12.43 ° / ^o; found:

C: 61%, H: 10.3%, N: 10.7%,

S: 12.8%.

Melting point: 130-134 ° C.

It has further been found that certain urea derivatives having a structure in which at least one alicyclic radical with at least three substituents - of which preferably two are in the geminal position - are present, can be used in particular as selective weed control agents. The structure of the urea derivatives according to the invention is novel and clearly differs from the known urea derivatives which are used as weed control agents.

The compounds of formula I have excellent high selectivity, inter alia, in winter wheat, winter cereals, rye, spring barley and spring wheat. Thus, these compounds are very effective, inter alia, against field fox (Alopecurus myosuroides), whiskers (Apera spica-venti), Stellaria media and Anthemis spec.

Compatibility by crop plants in spring cereals (oats, spring barley, spring wheat, etc.) is better than that of all comparative means. Especially in spring barley and oats, there are no effective soil herbicides with effect on field fox (Alopecurus myosuroides) and above all on broom (Apera spica-venti). This object is achieved in an excellent way by the compounds according to the invention. In winter wheat and in winter barley, pre-emergence (for both post-emergence and post-emergence) applications is suitable.

In addition, for post-emergence application it is preferred that this application can be carried out in combination with other herbicides (e.g. phenoxy fatty acids, triazines).

In view of the structure / activity relationship of the compounds of the invention, a fully saturated and highly substituted ring system is essential for selective herbicidal activity. The radical R3 in formula I plays a significant role in activity, especially when the two radicals are in the geminal position. If one geminal residue is replaced by a hydrogen atom at a lower substitution, for example by trisubstitution, then the activity is significantly reduced.

In addition, the compounds according to the invention are characterized by their ability to control growth, which results in an increase in the ripening time of the cereals. Due to the prolonged deposition of assimilate in the maturation grain, the protein content of the cereal grain is increased, among other things. Of particular importance for the activity of the compounds of formula I is the molecular bulklness of the molecule.

Thus, surprisingly, this effect manifests itself in the ability to regulate growth, in particular in the case of compounds in which the cyclohexyl radical is trans and which correspond to the general formula I.

H

[trans (eq, ax)]

The compounds of the formula I according to the invention which, when applied preemergence and postemergence, have a good herbicidal activity against a number of important grass weeds, on the other hand and at high doses, are well tolerated by dicotyledonous crops and various types of cereals. These compounds are excellently useful as antidotes for toxic herbicidal compositions and as components in admixture with known and important herbicides from the triazines, ureas and phenoxy fatty acids family, and are excellently useful for the production of broad spectrum herbicides with synergistic effect.

A great advantage of the compounds according to the invention. In addition to their surprisingly extraordinary effects and areas of application, the invention furthermore consists in the fact that they do not contain any halogen and hardly degradable groups which lead to problems [trans (ax, eq)] related to residues of these substances in the soil or plant.

Due to the compatibility with crop plants, the rapid action, the associated rapid degradation of the active compounds of the formula I and the absence of problems with residues of these substances in the soil or in the crop plant, there is no need for any environmental concern.

The active compounds of the formula I can be present in the compositions in an amount of from 2 to 95% by weight, in addition to the other components of the herbicidal compositions, and can be used in the form of various preparations.

Thus, the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble práš221280, granules, aerosols, suspension "or emulsion concentrates ^{pr ASK} y ^p ro sea ^{seed alkyl} acrylate effective im ^p regnované pnrodntai and synthetic Tett jataž and fine taps in ^p ol ^y mer téttach ^ lovatf and compositions for seed.

These formulations are known from the ^p Úsobí ^{to EXAMPLE Cart} la ^d snesením ^of active ^{E of a substance} with ^p lnidly te ^soil with ^k and ^p alnými extended ^p Oust ^d ly, liquefied gases under pressure, and no ^b o / and ^p evnými carrier tottamt, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents. In case of using water as an extender as may ^p · omocn ^and expanded Oust ^{EDL p} and ^p ou ^f Ivat Rik ^{P] d} i ^which just extended organic ^Inhalants and ^p ou.

Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or c ^hl orovan ^s aWaticta uhtovo ^ y as chlorobenezene, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as · acetone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents ^{STE d l} and ^d, as ^ methyformamid and dimethylsulphoxide, as well as water.

OF^toand^paln^Eným^{i ply}nnými^pBy fluids or carriers are meant liquids that are at normal temperature and normal pressure^toat^pFor example, aerosol filters such as hydrogenated hydrocarbons are^toož i bu tan, propane, nitrogen and^toysniční^to carbon dioxide. Suitable solid carriers are: natural^whereen^E my^čky, such as kaolins, alu ^^, talc,^toera, tasme ^ and ^ ta^phive^Git, montmorillonite or diatomaceous earth and synthetic^kanames, me^toabout high dis^perous acid^tořem^ičithose, alumina and quartz boats.

^Howo pevn^E nosn^{é lá}t^{ky p}ro^pr^praⁱⁿu gr^andzero^andt^at pnch^andzej^and considered crushed and fratty^nované pHodn^toamenn^E matertély^aslime^Enec, Marble pumice^, se^piolite and dot ^ j^ak°^{ž i} syntmta^GRanulát^y from organic and organic^toof my^Cek a^grand^nulath^y from organic matte, as from Gr^Ostork^{ek koko}Satⁱⁿýc^h of nuts^toukuřič^ných^Byeif^ca tab^ákovýc^h stems. Jata emuls^Gand it^ry No^{bo /}a zp^Emnidla mnidla^přicháze^jandⁱⁿ atⁱⁿahuⁿei^itgenn^{í a} Miomcta emulsifiers^Iand polyoxyethylene ester^y of fatty pitches^pO fatty lyoxyethylene ethers^andlkoh^Olů,^onp^saylad al^toylary^lpol^yglytaleth.er^, acid náty^andl^toylsul^Fstates, ar^ylsulfonate^ya h^ydrol^yzáthose whites and jata^disper^Gátor^y on^phe said^andd hgnrn, sulftové od^pand^dlye^ya methylce lulosis.

Prostrata ^{thanks to} the ^{p dl} ev ^y n and ^l can be contained cut ^h ovata Adhesives such as ethylcellulose Tarbox ^ ^ y an d ^d p ^of the ^P and R ^A synthetic ^ish, granules or latices, such as gum arabic ·, polyvlnylalkohol and polyvinylacetate.

Further, m ^a h ^about by these ^p rostrata ^{thanks to} contain 'tanh ^j ata anorganicta ^p igmenty ^on ^ P EXAMPLE ^alkyl pulcherrima ^Cart Z ^{e lez-characterized, alkyl} sl ^and protrudes ^toward útérnmty ^and ferrok ^y The amide mod ^r and orgamcta the dye ^I the alizarin dyestuffs tavov phthalate ^and up ^{to R)} C ^{y á} aninrv barvka and ^with it ^entrusts RVK ^{p y} ^ naj íktad method ELEZ ^{f, g and} m and n well, tar, copper-cobalt, ^d motyb ene zmta.

Krnmentráty general contain between 0.1 and 95% by weight-preferably between ^0, 5 ^and 90 · ^1% hmotnrstmm ^teaches nn ^é kitty.

Applications The active ingredient according to the invention ^p r ^{o r} fo Adi my jejtéh ^p rostrata ^{line examples} usual on the market and / or in the form of ^P and L and ^{also no} --N ^H pnpravků, which were prepared from the concentrated ^p rostrata ^{line examples.}

Content of active substance in dosage forms to be administered^pn^pravuj^and of^prostře^dků ob on the market, can be varied within wide limits. Concentration^atčmn^E The dosage forms may range from 0^,0000001 to 10% by weight.^Appace se^provádí z^půso^bem^exiz^pthe same application form.

The invention is further illustrated by the following examples: z ^p racování ^account innýc ^{h kp la} te ^ ro atactau application and the results of biological assays:

A water-dispersible wettable powder is obtained by mixing parts of the active substance, parts of highly dispersed silicic acid, parts of an emulsifier consisting of anionic and non-ionic surfactants, parts of a polyphosphate as a wetting agent and a dispersant and as a complexing agent, and grinding the resulting mixture suitable mill.

· The composition is then dispersed prior to application in water to the appropriate concentration used is used as an ^RA smámtétéý ^p e ^k.

Herbicidal effects of application of active substances:

and

Example 1 »

i. #^INe glass for the following preemergentaé plants (^pre] a^pif^toon^povrch^pat dy př^d Measured seeds and^postemer^Gpostntam on^pof the leaves^and double and double^worksO^ofgrowing in the stern of 1st leaf^aujE^dno^worksO^ofplants in the 3rd part^,compounds. listed^E in the following tab^attée 1 j^akožtExamples of compounds^podle^vynbut^{zu v} quantity 4^kg at^whoseper hour^vzt^toeno n^and vengeance^substance sus^pendowedⁱⁿ 1200 htrech vo^dy/ ha.

The effect of the preparations is evaluated three weeks after treatment. In the Table, the evaluation ^or tool number 1 ^p p & LNY EQS i.e. zniišem hod221280 ation numeral 5 indicates no effect, i.e. the plants are the same as the untreated plants ·.

Table 2 shows the results for the comparative means.

Table 1 ^P by the environment and community ^{ky y} n and ^l Rajs ^Ké Fit cut oats apple ore post pre post pre oats blackgrass post pre post pre post

1- (3,3,5-trimethyl lcyklohex ^{y Y} R) -3,3-dimethylurea (cis orma ^{f) 11 1}

1- (3,3,5-trimethyl-cyclohex ^yl) - ^{3, 3 -dimethyl-yl urine} ovma ^{11 1-} (trans-form)

1- (thylcyclohexyl) -3,3-dimethylthiourea 11 1 (cis-form)

The results using compounds of the invention exhibit 3 weeks after treatment for ^no good ^EFFECTIVE p ^{s p g} reemer entmm ^and post-emergence treatment test in dvojdě-

1 2,5 4 2 3,5 1 1 12 2 1 1,5 1 1 1 2 3 ' 2 2 1 1 loading plant. Cis-form above listed the compound is in postemergence application

^SN §ena well of course.

Table 2 comparative tomato mustard oats oat deaf foxtail apple pre pos pre post pre post pre post pre post 1-cyclohexyl ^^ - dimethylurea1

1- [ ^3- Chloro-4-methyl-urea] -3,3-dimethylurea1 (Dicuran)

1112 11 1

2. 1 11 1

N botanists ^and increases pourivaných rostlrn:

tomato mustard oats oats deaf foxtail

Solanum lycopersicum

Sinapsis alba

Avena sativa

Avena fatua

Alopecurus myosuroides

Example 2 and post-emergence (post) applying to said different rostlmách tested compounds of the invention listed in Tables 3 and 4, the applied amount of 4 · 3, 2 and 1 kg of active substance / ha, based · on ^taught purely nnou Ut ^ sus ^p ending in 1200 liters of water per hectare.

Tables 5 and 6 contain the results for the comparative means.

Legend: otherwise as in Table 1.

In the greenhouse at pre-emergence (pre)

Table 3 herbicidal effect of test plant 1- (3,3,5-trimethylcyclohexyl) -3,3-dimethylurea, cis-form applied amount in kg of active substance per ha

3 4

mustard for 1 1 1 1 post 1 1 1 1 tomato for 1 1 1 1 post 1 1 1 1 hedgehog corns the leg for 2 2 1 1 post 4 2 1 1 oat for 5 3 2.5 2.5 post 5 3 1.5 1 oat deaf for 2 1 1 1 post 3.5 2 1 1 Psař polní for 2 1 1 1 post 1 1 1 1 chickweed frog for 2 1 1 1 post 2 1.5 1 1 cornflower blueprint for 4 2.5 1 1 post 4 4 2 1 rmen for 1 1 1 1 post 1.5 1 1 1 goosefoot white for 1 1 1 1 post 3 1 1 1 chundelka metlice for 1 1 1 1 post 1 1 1 1 spring barley for 4 4 3 1.5 post 3 3 3 2.5 spring wheat for 4,5 4 3 1.5 post 3 2 1.5 1 soya for 4,5 4,5 3 2.5 post - - - - cotton for 3 3 3 3 post 5 5 4,5 4

Table 4 herbicidal effect of test plant 1- (3,3,5-trimethylcyclohexyl) -3,3-dimethylinurea, trans-form applied amount in kg of active substance per ha

3 4

mustard for 1 1 1 1 post 1 1 1 1 tomato for 1 1 and· 1 post 1 1 1- 1 hedgehog corns the leg for 2 1 1 1 post 3 2 1 1 oat for 2 2 2.5 1 post 2 2 2 1 oat deaf for 1 1 1 1 post 1.5 1 1 1 Psař polní over 1 1 1 1 post 1 1 1 1 chickweed frog for 1 1 1 1 post 1 1 1 1 cornflower blueprint for 3 1 1 1 post 3 3 2 1 rmen for 1 1 1 1 post 1 1 1 1 goosefoot white for 1 1 1 1 post 1 1 1 1

test plants herbicidal effect of 1- (3,3,5-triin-thiylcyclohexyl) -3,3-climetliylurea: trans-form applied amount in kg of active substance per ha

3 4

chundelka metlice for 1 1 1 1 . .., g ^ iPOSt 1 1 1 1 spring barley for 4 4 3 1 post 3 3 3 1 spring wheat for 4 4 2 1.5 5 'post 3 3 1 1 soya for 4,5 4 3.5 3.5 post - - - - cotton for 2 2 1 1 post 4 4 4 2

The compounds of the invention are well tolerated in spring doses by spring cereals.

us (spring barley, tested plants spring wheat, oats). Table 5 - Comparative means - herbicidal effect of 1-cyclohexyl-3,3-dimethylurea 1 ha 4 amount applied i '1 in kg of active substance per 2 3 mustard over 1 1 1 1 post 1 1 1 1 tomato for 1 1 1 1 post 1 1 1 1 hedgehog corns the leg for 2 2 1 1 post 4 4 1 1 oat for 2 1 1 1 post 3 3 1.5 1 oat deaf for 2 1 1 1 post 2 1 1 1 Psař polní for 1 1 1 1 post 1 1 1 1 chickweed frog for 2 1 1 1 post 2 1.5 1 1 cornflower blueprint for 4 2 1 1 -. . post 3 3 2 1 rmen for 1 1 1 1 post 1 1 1 1 goosefoot white for 1 ....... 1 1 1 post 1 1 1 1 chundelka metlice for 1 1 1 1 * - i 'post 1 1 1 1 spring barley for 2.5 2.5 2 1 ;; '.' / post 4 4 3 1 spring wheat for 2 2.5 1.5 1.5 post 4 3 1 1 soya for 5 4,5 3.5 3.5 post - - - - cotton for 2.5 1 1 1 post 4 1 1 1

Table 6 comparative herbicidal effect

1- (3-chloro-4-methylphenyl) -3,3-dimethylurea of the test plant

Dicuran

application rate in kg of active substance per ha 1 2 3 4 mustard for 1 1 1 1 post 1 1 1 1 tomato for 1 1 1 1 post 1 1 1 1 hedgehog corns the leg over 1.5 1 1 1 post 2 1 1 oat for 1 1 1 1 post 1 1 1 1 oat deaf for 2.5 1 1 1 post 1.5 1 1 1 Psař polní for 1 1 1 1 post 1 1 1 1 chickweed frog for 1 1 1 1 post 1 1 1 1 cornflower blueprint for 2.5 1 1 1 post 3 1 1 1 rmen for 1 1 1 1 post 1 1 1 1 goosefoot white for 1 1 1 1 post 1 1 1 1 chundelka metlice ! for 1 1 1 1 post 1 1 1 1 spring barley for 1.5 1 1 1 post 1.5 1 1 1 spring wheat for 2 1.5 1 1 post 2 1 1 1 soya for 2 1 1 1 post - - - - cotton over 3 3 2 1 post 3 2 1 1 Botanical names of plants used: cornflower blueprint Centaurea cyanus rmen Anthemis spec. mustard Sinapsis alba goosefoot white Chenopodium album tomato Solanum lycopersicum Apera spica-venti hedgehog corns the leg Echinochloa crus-galli barley Hordeum vulgare oat Avena sativa wheat Triticum aestivum oat deaf Avena fatua soya Soybean Hispida Psař polní Alopecurus myosuroídes cotton Gossypium hirsutum

Chickweed Stellaria media

Claims (4)

OBJECT OF THE INVENTION A herbicidal composition, characterized in that it contains at least one urea derivative of the formula I as active ingredient R ² OF R - NR @ 1 - C - N (Ij in which R is du 1, of the formula I, characterized in that it is a compound of the formula R —A in which X is oxygen or sulfur; and R ¹ represents hydrogen or methyl, R2 and ^R3 are the same or different, each are hydrogen, methyl, methoxy or phenyl. 2. A composition according to claim 1, characterized in that it comprises as active ingredient at least one urea of the formula I in which at least two ring substituents in the radical R are trans and R, X, R ^1, R ^2, and R ³ have the meanings given in point 1. 3. A composition according to claim 1, characterized in that it comprises as active ingredient at least one urea derivative of the formula I wherein R is 3,3,5-trimethylcyclohexyl а radical X, R ^1, R ² and R ³ have the meanings indicated in point 1. 4. The process for the preparation of the active ingredient according to the invention is treated with compounds of the general formula R ² \ N — В, where either A is NCO or NCS; and V is hydrogen, or A is-NR ^1a В is COC1 or CSC1, and R ¹ , R ² , R ³ and R ³ are as defined in general formula I in point 1.