Derivatives of 2-amino-1,3,5-triazine, herbicide agent based on thereof and method for control of hazard plants

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes derivatives of 2-amino-1,3,5-triaziene of the formula (I): wherein R1 means phenyl or alkyl with from 1 to 6 carbon atoms that can be substituted with one or some radicals taken among halogen atom and cyano-group; R2 means unsubstituted cyclopropyl, cyclobutyl or cyclopentyl groups or substituted that with radical taken among halogen atom and alkyl with from 1 to 4 carbon atoms, or furyl, or tetrahydrofuryl; R3 means radical of the formula -N(B1-D1)(B2-D2); R4 means radical of the formula -B3-D3; A1 means direct alkylene with 1-5 carbon atoms or direct alkenylene with 2-5 carbon atoms; A2 means a direct bond or direct alkylene with 1-4 carbon atoms; B1, B2 and B3 mean a direct bond; D1, D2 and D3 mean hydrogen atom; (X)n means a number of X substitutes wherein X means independently halogen atom, nitro-group or unsubstituted alkyl with 1-6 carbon atoms or substituted that with one or some radicals taken among halogen atom and alkoxy-group with 1-6 carbon atoms; n = 0, 1 or 2 and wherein the total sum of carbon atoms in radicals A1 and A2-R2 is at least 6 carbon atoms. Also, invention describes the herbicide agent containing compound of the formula (I) and additives used usually for plants protection and a method for control of hazard plants and using the effective dose of compound of the formula (I) for treatment of plants or planting surface. Invention provides preparing effective herbicides.

EFFECT: valuable properties of compounds.

7 cl, 45 tbl, 4 ex

 

The invention relates to the field of plant protection products, such as herbicides and plant growth regulators, especially herbicides for selective control of noxious plants technical crops.

It is known that 2-amino-4-(N-phenylalkyl-amino)-1,3,5-triazine, substituted in position 6, which can be substituted further, have a weed-killing properties and regulate the growth of plants; see international application WO 97/08156 and are there links, international application WO 98/15537 and are there links; international application WO 97/00254 and are there links.

When using the known biologically active substances are such deficiencies as lack of herbicide action against harmful plants, too low spectrum of harmful plants, which can compete with the active substance, or too low selectivity in commercial crops. Economical production of other active substances on an industrial scale is impossible due to the complicated obtain primary products and reagents, or derived biologically active substances have a short chemical stability.

The objective of the proposed invention is to provide an alternative active substances such as 2,4-diamino-1,3,5-triazines, which are most preferably can be used in quality is as herbicides and plant growth regulators.

The object of the proposed invention are the compounds of formula (I) and their salts

in which

R1is aryl, which is unsubstituted or substituted and existing substituents are preferably 6-30 carbon atoms, or cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted and existing substituents are preferably 3-30 carbon atoms, or heterocyclyl, which is substituted or unsubstituted and existing substituents preferably have 2 to 30 carbon atoms, or alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms or quinil with 2-6 carbon atoms,

each of the three last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkenylacyl with 2-4 carbon atoms, haloalkoxy with 2-4 carbon atoms, alkylthio with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, haloalkaline with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms and

cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted, and phenyl, which is unsubstituted or substituted, a heterocycle, which is unsubstituted or substituted, and radicals of the formulae R’-C(=Z’), ’-C(=Z’)-Z-, R’-Z-C(=Z’)-, R R’N-C(=Z’)-, R’-Z-C(=Z’)-O-, R R"N-C(=Z’)-Z-, R’-Z-C(=Z’)-NR’- and R R’N-C(=Z’)-NR’"-, where R’, R’ and R’’ independently are alkyl with 1-6 carbon atoms, aryl, aryl(C1-C6)alkyl, cycloalkyl with 3-9 carbon atoms or (C3-C9-cycloalkyl-(C1-C6)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted, and Z and Z’ independently represent an oxygen atom or sulphur,

and existing substituents are preferably 1-30 carbon atoms,

R2is cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted, cycloalkenyl with 4-9 carbon atoms, which is unsubstituted or substituted, heterocyclyl, which is unsubstituted or substituted, or phenyl which is unsubstituted or substituted, at the same time acting substituents R2have preferably up to 30 carbon atoms, or

R3is hydrogen, alkyl with 1-6 carbon atoms, aryl or cycloalkyl with 3-9 carbon atoms, and each of the three last mentioned radicals is unsubstituted or substituted, or a radical of the formula-N(B1-D1)(B2-D2or-NR’-N(B1-D1)(B2-D2where1In2D1and D2such as defined below, and R’ is hydrogen, alkyl with 1-6 carbon atoms, or [(C1-C4)alkyl]-carbonyl, and the current replacement is the Fort worth R 3have preferably up to 20 carbon atoms,

R4is a radical of the formula-In3-D3and In3and D3such as defined below, and existing substituents R4have preferably up to 20 carbon atoms,

And1is a direct alkylene with 1-5 carbon atoms or a direct Alcanena or akinlana with 2-5 carbon atoms, and each of the three last named of diradicals unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, thiocyanato and radicals of the formula-B4-D4and In4and D4such as defined below,

And2is a direct bond or a straight alkylene with 1-4 carbon atoms or a direct Alcanena or akinlana with 2-5 carbon atoms, and each of the three last named of diradicals unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, thiocyanato and radicals of the formula-B5D5; or divalentin the radical of the formula V1, V2, V3, V4or V5,

-CR6R7-W*CR8R9(V1)

-CR10R11-W*CR12R13-CR14R15(V2)

-CR16R17-CR18R19-W*CR20R21(V3)

-CR22R23-CR24R25-W* (V4)

-CR26R27 -W* (V5)

moreover, each of the radicals R6-R27independently is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula-B6-D6, W is oxygen atom, sulfur or a group of the formula N-(B7-D7and

In5In6In7D5D6and D7such as defined below,

In1In2In3and7independently are a direct bond or divalent group of formula-C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH - or-C(=Z*)-NR*-, where Z* is an oxygen atom or sulfur, Z** is an oxygen atom or sulfur and R* is alkyl with 1-6 carbon atoms, aryl, aryl-(C1-C6)alkyl, cycloalkyl with 3-9 carbon atoms or (C3-C9)cycloalkyl-(C1-C6)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted and existing substituents preferably have up to 20 carbon atoms,

In4In5and6independently are a direct bond or divalent group of formula-O-, -S(O)p-, -S(O)p-O-. -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NRo-, -O-NRo-, -NRo-O-, -NRo-CO-, -CO-NRo-, -O-CO-NRo- or-NRo-CO-O-, and p is an integer 0, 1 or 2 and R° is hydrogen, alkyl with 1-6 carbon atoms, aryl, aryl-(C1-C6)alkyl, cyclea the kilometres with 3-9 carbon atoms or (C 3-C9)cycloalkyl-(C1-C6)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted, and existing substituents preferably have up to 20 carbon atoms,

D1D2D3D4D5and D6independently are hydrogen, alkyl with 1-6 carbon atoms, aryl, aryl-(C1-C6)alkyl, cycloalkyl with 3-9 carbon atoms or (C3-C9)cycloalkyl-(C1-C6)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted, and existing substituents preferably have up to 20 carbon atoms; or two radicals D5of the two groups-B5-D5that are linked by a carbon atom, are connected to each other and form a group of alkylene with 2-4 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group of alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms,

(X)n- n substituents X and X independently is halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkylthio with 1-6 carbon atoms, mono(C1-C6)alkylamino, di(C1-C4)alkylamino, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, [(C1-C6)is lcil]carbonyl, [(C1-C6)alkoxy]carbonyl, mono(C1-C6)alkylamino-carbonyl, di(C1-With4)alkylamino-carbonyl, N-(C1-C6)alkanoyl-amino or N-(C1-C4)alkanoyl-N-(C1-C4)alkyl-amino,

each of 13 last mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, (C3-C9)cycloalkyl-amino, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbinol, heterocyclyl, heterocyclic, heterocyclic, heterocyclisation, and each of the 8 last-mentioned radicals is unsubstituted or has one or more substituents from the group halogen, nitro, cyano, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 atom and carbon, of formyl, (C1-C4)alkylsulphonyl and (C1-C4)alkoxy-carbonyl, or cycloalkyl with 3-9 carbon atoms, cycloalkane with 3-9 carbon atoms, cycloalkenyl with 3-9 carbon atoms, phenyl, phenoxy, phenylthio, phenylcarbinol, heterocyclyl, heterocyclic, heterocyclic or heterocyclisation,

each of the 11 last-mentioned substituents, unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, amino-carbonyl, mono(C1-C4)alkylamino-carbonyl and di(C1-C4)alkylamino-carbonyl,

or two adjacent radicals X together are unfused cycle with 4-6 ring atoms, which is carboxyl, or contains a ring heteroatoms from the group O, S and N and which is unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1 to carbon atoms and oxo,

n is 0, 1, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, most preferably 1 or 2, and

heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3-7 ring atoms and 1-3 heteroatoms from the group N, O and S,

and

(a) the total amount of carbon atoms in the radicals And1and A2-R2is at least 6 carbon atoms or

b) the total amount of carbon atoms in the radicals And1and A2-R2makes 5 carbon atoms and a1is a group of formula-CH2- or-CH2CH2-, and R1is an alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkyl with 2-6 carbon atoms or cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted.

If not specified in more detail, divalent radicals, such as1=-C(=Z*)-Z**-, determined in such a way that constituted groups, such as-B1-D1such communication divalent radicals has been linked to group D1that in the formula for devalentino radical recorded to the right, i.e. B1-D1is a group of the formula-C(=Z*)-Z**-D1; respectively define similar divalent radicals.

The compounds of formula (I) can form salts by attaching a suitable inorganic or organic acid, nab the emer Hcl, NVG, H2SO4or NGO3and also oxalic acid or sulfonic acids, to basic group such as amino or alkylamino. Suitable substituents that are in deprotonated form, such as sulfonic acid or carboxylic acids, can form internal salts with groups capable of protonation, for example amino groups. Salt can also be formed by a method by which under suitable substituents such as sulfonic or carboxylic acids, the hydrogen is replaced by a cation, suitable for use in agriculture. These salts are, for example, metal salts, preferably alkali metal salts or salts of alkaline-earth metals, preferably sodium and potassium salts, but also ammonium salts, salts with organic amines or Quaternary ammonium salts.

In the formula (I) and all subsequent formulae, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, alkylthio, and also the corresponding unsaturated and/or substituted radicals in the carbon skeleton may be straight or branched. Unless otherwise specified, in these preferred radicals are the lower carbon skeletons, for example, with 1-6 carbon atoms or, when unsaturated group with 2-6 carbon atoms. The alkyl radicals, also in the meaning of alkoxy, haloalkyl and dragicevica, for example, stands, ethyl, n - or ISO-propylene, n-, ISO-, tert - or 2-bootrom, pentiumi, hexylene, for example n-hexyl, ISO-hexyl and 1,3-dimethylbutyl, heptylene, such as n-heptyl, 1-methylhexan and 1,4-dimethylpentyl; the radicals alkenyl and quinil are unsaturated radicals corresponding to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-EN-1-yl, 2-methyl-prop-2-EN-1-sludge, but-2-EN-1-yl, but-3-EN-1-yl, 1-methyl-but-3-EN-1-yl and 1-methyl-but-2-EN-1-yl; quinil is, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-Il.

Cycloalkyl is carbocyclic, saturated ring preferably 3-8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Substituted cycloalkyl is cyclic system substituents, and the substituents are connected by a double bond with the radical cycloalkyl, for example, a group of alkylidene, such as methylidene. Substituted cycloalkyl is also cyclical aliphatic system, for example, bicyclo[1.1.0]butane-1-yl, bicyclo[1.1.0]butane-2-yl, bicyclo[2.1.0]pentane-1-yl, bicyclo[2.1.0]pentane-2-yl, bicyclo-[2.1.0]pentane-5-yl, adamantane-1-yl and adamantane-2-yl.

Cycloalkenyl is carbocyclic, not aromatic, partially unsaturated ring, preferably 4-8 carbon atoms, nab the emer 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substituted cycloalkenyl use definitions substituted cycloalkyl.

Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkyl and haloalkyl are alkyl, alkenyl or quinil, such as monocalcium (=monohalogenated), pengelolaan, CF3, CHF2CH2F, CF3CF2CH2FCHCl, CCL3, l2CH2CH2CL, partly or completely replaced by halogen, preferably fluorine, chlorine and/or bromine, most preferably fluorine or chlorine; haloalkoxy is, for example, F3, OCHF2, OCH2F, CF3CF2O co2CF3and co2CH2CL; these definitions correspond haloalkenes and other radicals substituted with halogen.

Aryl is a mono-, bi - or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenolol, indenolol, pentolinium, florinela and the like, preferably phenyl.

Heterocyclics radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; preferably it contains the Dean or more, preferably 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O and S; preferably it is an aliphatic radical heterocycle with 3-7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), for example, mono-, bi - or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, or is partially or fully gidrirovanny radical, such as oxiranyl, oxetanyl, oxyanion (=tetrahydrofuryl), oxania, pyrrolidino, piperidino, piperazinil, DIOXOLANYL, oxazolidines, isoxazolyl, oxazolidinyl, isoxazolidine and morpholinium. As Vice-substituted heterocyclic radical use nienazwane deputies, also oxo. The carbonyl group can also be at the ring heteroatoms, which may be present in various stages of oxidation, for example, atoms N and S.

Substituted radicals, for example substituted alkyl radical, alkenyl is, the quinil, aryl, phenyl, benzyl, heterocyclyl and heteroaryl are, for example, a substituted radical derived from the unsubstituted basis, and the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylsulphonyl, formyl, carbamoyl, mono - and dialkylaminoalkyl, substituted amino, for example, acylamino, mono - and dialkylamino, and alkylsulfonyl, haloalkylthio, alkylsulfonyl, haloalkylthio and, in the case the use of cyclic radicals, alkyl and haloalkyl; the term “substituted radicals”, such as substituted alkyl as substituents addition to the above-mentioned saturated radicals containing hydrocarbon includes corresponding unsaturated aliphatic and aromatic radicals, for example, in this case, replaced alkenyl, quinil, alkenylacyl, alkyloxy, phenyl, phenoxy. Substituted cyclic radicals with aliphatic components of the ring are also cyclic systems with substituents that are associated with the ring double bond, for example a group of alkylidene, such as methylidene or ethylidene.

When the radicals with the carbon atoms are preferred radicals with 1-4 atoms ug is erode, most preferably with 1 or 2 carbon atoms. Preferred substituents are, as a rule, are, for example, substituents from the group halogen, for example fluorine and chlorine, alkyl with 1-4 carbon atoms, preferably methyl or ethyl, haloalkyl with 1-4 carbon atoms, preferably trifloromethyl, alkoxy with 1-4 carbon atoms, preferably methoxy or ethoxy, (C1-C4)haloalkoxy with 1-4 carbon atoms, nitro and cyano. The most preferred substituents are methyl, methoxy and chlorine.

Mono - or disubstituted amino is a chemically stable radical from the group of the substituted amino radicals which are N-substituted, for example by one or two identical or different radicals from the group of alkyl, alkoxy, acyl and aryl; preferably monoalkylamines, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino, and N-heterocycles; and most preferable are alkyl radicals with 1-4 carbon atoms; and aryl is preferably phenyl or substituted phenyl; and acyl are the following definitions, preferably (C1-C4)alkanoyl. Accordingly define substituted hydroxylamine or hydrazine.

In this case, the substituted phenyl is preferably phenyl which is unsubstituted or once or megatr the IDT, preferably up to three times substituted by identical or different radicals from the group halogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogenoalkane with 1-4 carbon atoms, halogenoalkane with 1-4 carbon atoms and nitro, for example o-, m - and p-tolyl, dimethylphenyl, 2-, 3 - and 4-chlorophenyl, 2-, 3 - and 4-Cryptor - and-trichlorophenyl, 2,4-, 3,5-, 2,5 - and 2,3-dichlorophenyl, o-, m - and p-methoxyphenyl.

The aryl radical is the radical of an organic acid, for example a radical of carboxylic acid and radicals of its derivatives, for example thiocarbonate acid, in this case, the N-substituted aminocarbonyl acid or the radical of complex monoether carbonic acid, in this case, the N-substituted karamanova acid, sulfonic acid, sulfinate acid, phosphonic acid, phosphinic acid. Acyl is, for example, formyl, alkylcarboxylic, for example, [(C1-C4)alkyl]-carbonyl, phenyl-carbonyl, allyloxycarbonyl, vinyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfonyl, N-alkyl-1-aminoalkyl and other radicals of organic acids. Moreover, the radicals in the part of the alkyl or phenyl can be substituted further, for example, in parts of alkyl by one or more radicals from the group halogen, alkoxy, phenyl, phenoxy; substituents in parts of phenyl are already above substituents for Sames the frame phenyl.

The subject invention are all stereoisomers, which contains the formula (I), and mixtures thereof. Such compounds of formula (I) contain one or more asymmetric carbon atoms or a double bond shown in formula (I). Formula (I) includes stereoisomers defined by their specific stereochemical form, such as enantiomers, diastereomers, Z and E isomers, which can be obtained by customary methods from mixtures of the stereoisomers or by stereoselective reactions in combination with the use of stereochemical pure starting materials.

The proposed connection of the mentioned formula (I) or their salts, especially, are most preferred because of higher herbicide action, improved selectivity and/or easier to obtain, in which the individual radicals have already been specified or indicated in the following preferred definitions, or particularly preferred compounds are those in which can be used in combination of one or more named or following named preferred definitions.

R1preferably is phenyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, alkyl with 1 to 4 atoms of carbon is a, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, (C3-C9)cycloalkyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, (C1-C4)alkylsulfonyl and (C1-C4)-haloalkylthio, and acting Deputy have 6-30 carbon atoms, preferably 6-20 carbon atoms, most preferably 6 to 15 carbon atoms.

R1also preferably is cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino and di(C1-C4)alkylamino, and acting Deputy have 3-30 carbon atoms, preferably 3-20 carbon atoms, most preferably 3-15 carbon atoms.

R1also preferably is heteros what cyclelab, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, amino-carbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, (C1-C4)alkylsulfonyl and (C1-C4)haloalkylthio, and acting Deputy have 2 to 30 carbon atoms, preferably 2-20 carbon atoms, most preferably 2 to 15 carbon atoms.

And also other radicals heterocyclyl is preferably a heterocyclic radical having 3-7, preferably 3-6, ring atoms and one heteroatom from the group N, O and S, such as pyridium, teinila, fullam, pirrallo, oxiranyl, oxetanyl, oxyanion (=tetrahydrofuryl), oxania, pyrrolidino, piperidino, or heterocyclic radicals with two or three heteroatoms from the group of pyrimidyl, pyridazinyl, pyrazinyl, triazine is a, tanila, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinil, DIOXOLANYL, oxazolyl, isoxazolyl, oxazolidinyl, isoxazolidine, morpholine.

R1also preferably is alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms or quinil with 2-6 carbon atoms, and each of the three last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkenylacyl with 2-4 carbon atoms, haloalkoxy with 2-4 carbon atoms, alkylthio with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, (C1-C4)alkylsulfonyl, halo-alkylsulfonyl with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, and cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino and di(C1-C4)alkylamino; and phenyl and heterocyclyl, each of the last two on the bathrooms radicals unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms; and radicals of the formulae R’-C(=Z’)-, R’-C(=Z’)-Z-, R’-Z-C(=Z’)-, R R’N-C(=Z’)-, R’-Z-C(=Z’)-O-, R R’N-C(=Z’)-Z-, R’-Z-C(=Z’)-NR’- and R R’N-C(=Z’)-NR’-, where R’, R’ and R’’ independently are alkyl with 1-4 carbon atoms, phenyl, phenyl(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6-cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, alkenyl with 2-4 carbon atoms, an alkyne is La with 2-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, and in the case of cyclic radicals, also alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, a Z and Z’ independently represent an oxygen atom or sulfur, and existing substituents are preferably 1-20 carbon atoms, most preferably 1-15 carbon atoms.

R1preferably is an alkyl with 1-4 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, alkylsulfonyl with 1-4 carbon atoms, cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted; and phenyl, which is unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, amino, mono - and di[(C1-C4)alkyl]amino, (C1-C4)alkanolamine, benzoylamine, nitro, cyano, [(C1-C4)alkyl]carbonyl, formyl, carbamoyl, mono - and di[(C1-C4)alkyl]aminocarbonyl and alkylsulfonyl with 1-4 carbon atoms; and heterocyclyl with 3-6 ring atoms and 1-3 ring heteroatoms from the group N, O and S, where the ring is unsubstituted or substituted by one or more radicals from the group of halo is s, of alkyl with 1-4 carbon atoms, and oxo; or phenyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms, and acting Deputy have 2 to 30 carbon atoms, preferably 2-20 carbon atoms, most preferably 2 to 15 carbon atoms.

R1also preferably is an alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, benzyl or [(C3-C6)cycloalkyl]-(C1-C2)alkyl, preferably alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, or [(C3-C6)cycloalkyl]-stands, preferably-CH3, -CH2F, -CHF2, -CF3, -CH2Cl, -CHCl2, -CCl3-CH2 VG, -ADHD2, -CH2CH3, -CH2CH2F, -CF2CHF2, -CH2CH2CL, -CH2CH2Sh, -CH(CH3)2, -CF(CH3)2- (CH3)2CL, -CH2CH2CH2F, -CH2CH2CH2CL or cyclopropylmethyl.

Regardless of the radicals R1, R3, R4, A1And2and (X)nand preferably in combination with preferred meanings of one or more of these radicals are most preferred are the following values of R2:

R2preferably is cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group of A), B), C) and D), and

group a consists of the radicals halogen, hydroxy, amino, nitro, formyl, carboxy, aminocarbonyl, sulfo, cyano, thiocyanato and oxo,

group B consists of alkyl radicals with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, alkylthio with 1-6 carbon atoms, mono(C1-C6)alkylamino, di(C1-C4)alkylamino, alkenyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, cycloalkyl with 3-9 carbon atoms, cycloalkenyl with 4-9 carbon atoms, alkylidene with 1-6 carbon atoms, cycloalkene with 4-9 carbon atoms, radicals of the formulae R’-C(=Z’)-, R’-C(=Z’)-Z-, R’-Z-C(=Z’)-, R R’N-C(=Z’)-, R’-Z-C(=Z’)-O-, R R’N-C(=Z Is The)-Z-, R’-Z-C(=Z’)-NR’- and R R’N-C(=Z’)-NR’-, where R’, R’ and R’’ independently are alkyl with 1-6 carbon atoms, phenyl, phenyl(C1-C6)alkyl, cycloalkyl with 3-9 carbon atoms or (C3-C9-cycloalkyl-(C1-C6)alkyl, and Z and Z’ independently represent an oxygen atom or sulphur,

the group consists of the radicals of group B), each radical substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, cycloalkyl with 4-9 carbon atoms, cycloalkene with 4-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenyl-carbonyl, heterocyclyl, heterocyclic, heterocyclic, heterocyclisation,

each of the 21 last-mentioned radicals unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, ha is alkoxy with 1-4 carbon atoms, of formyl, (C1-C4)alkyl-carbonyl and (C1-C4)alkoxy-carbonyl and, in the case of cyclic radicals, also alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms and alkylidene with 1-6 carbon atoms,

and, in the case of cyclic radicals, also alkyl with 1-6 carbon atoms, haloalkyl with 1-6 carbon atoms and alkylidene with 1-6 carbon atoms, and

the group G consists of divalent and trivalent aliphatic bridges with 1-6, preferably 1-4, carbon atoms, which, in the case divalent bridges that connect two carbon atom cyclic basis or, in the case of trivalent bridges that link the three carbon atoms of the cyclic basis, and the radical R2is a radical Bicycle or tricycle, and each of these bridges unsubstituted or substituted by one or more substituents from the group halogen, nitro, cyano, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, (C1-C4)alkyl-carbonyl, (C1-C4)alkoxy-carbonyl and oxo, and where applicable, the substituents R2have 3-20 carbon atoms, preferably from 3 to 15 carbon atoms. And as radical cycloalkyl with 3-9 carbon atoms are preferred cyclopropyl, cyclobutyl, the CEC is opentel or cyclohexyl, most preferred are cyclopropyl, cyclobutyl or cyclopentyl.

R2also preferably is cycloalkenyl with 4-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group of radicals A), B), C) and D), for example, they are defined as radical if R2= cycloalkyl with 3-9 carbon atoms, and at the same time operating the substituents preferably have 4 to 20 carbon atoms, most preferably 4 to 15 carbon atoms. And as radical cycloalkenyl with 4-9 carbon atoms are preferred 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl and 3-cyclopentenyl.

R2also preferably is heterocyclyl, which is unsubstituted or substituted by one or more radicals from the group of radicals A), B), C) and D), for example, they are defined as radical if R2= cycloalkyl with 3-9 carbon atoms. And heterocyclyl is preferably a heterocyclic radical with 3-6 ring atoms from the group of pyridyl, teinila, furil, pyrrolyl, oxiranyl, 2-oxetanyl, 3 - oxetanyl, oxolane (=tetrahydrofuryl), pyrrolidyl, piperidyl, preferably of oxiranyl, 2-oxetanyl, 3 - oxetanyl or oxolane; or heterocyclic radicals with two or three heteroatoms, for example, pyrimidinyl, PI is Yasinya, pyrazinyl, triazinyl, teinila, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinil, DIOXOLANYL, oxazolyl, isoxazolyl, oxazolidinyl, isoxazolidine or morpholinyl.

R2also preferably is phenyl, which is unsubstituted or substituted by one or more radicals from the group of radicals A), B), C) and D), for example, they are defined as radical if R2= cycloalkyl with 3-9 carbon atoms.

Acting Deputy R2have preferably up to 20 carbon atoms, preferably up to 15 carbon atoms, most preferably up to 10 carbon atoms.

R2also preferably is cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group of A), B), C) and D), and

group a consists of the radicals halogen, hydroxy, amino, nitro, formyl, aminocarbonyl, cyano and thiocyanato,

group B consists of alkyl radicals with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, alkenyl with 2-4 carbon atoms, quinil with 2-4 carbon atoms, cycloalkyl with 3-6 carbon atoms, cycloalkenyl with 4-6 carbon atoms, alkylidene with 1-4 carbon atoms, cycloalkene with 4-6 atoms ug is erode, radicals of the formulae R’-C(=Z’)-, R’-C(=Z’)-Z-, R’-Z-C(=Z’)-, R R’N-C(=Z’)-, R’-Z-C(=Z’)-O-, R R’N-C(=Z’)-Z-, R’-Z-C(=Z’)-NR’- and R R’N-C(=Z’)-NR’-, where R’, R’ and R’’ independently are alkyl with 1-4 carbon atoms, phenyl, phenyl(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6-cycloalkyl-(C1-C6)alkyl, and Z and Z’ independently represent an oxygen atom or sulphur,

the group consists of the radicals of group B), each radical substituted by one or more radicals from the group halogen, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-6 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbinol, heterocyclyl, heterocyclic, heterocyclic and hetero-ciclamino,

each of the 8 last-mentioned radicals is unsubstituted or substituted by radicals from the group halogen, nitro, cyano, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 atoms is carbon, (C1-C4)alkyl-carbonyl and (C1-C4)alkoxy-carbonyl, and

the group G consists of divalent aliphatic bridges that connect the two carbon atoms of the cyclic basis, and as a consequence, the radical R2is a radical Bicycle, for example bicyclo[1.1.0]butane-1-yl, bicyclo[1.1.0]butane-2-yl, bizik-lo[2.1.0]pentane-1-yl, bicyclo[2.1.0]pentane-2-yl or bicyclo[2.1.0]pentane-5-yl, each of the bridges unsubstituted or substituted by one or more substituents from the group halogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 atoms carbon (C1-C4)alkyl-carbonyl, (C1-C4)alkoxy-carbonyl and oxo.

R2most preferable is cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 2-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, alkylidene with 1-4 carbon atoms, mono(C1-C4)alkylamino and di(C1-C4)alkylamino; or heterocyclyl or phenyl, and each of the two last named happy who calow unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-6 carbon atoms, heterocyclyl with 3-6 ring atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms.

Regardless of the radicals R1, R2, R4, A1And2and (X)nand preferably in combination with preferred meanings of one or more of these radicals are most preferred are the following values of R3:

R3is, for example, hydrogen, alkyl with 1-4 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino and di(C1-C4)and is calamine; or phenyl or cycloalkyl with 3-6 carbon atoms, and each of the two last mentioned radicals are unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms; or a radical of the formula N(B1-D1)(B2-D2), and1In2D1and D2such as already defined, or preferably such, as hereinafter defined, preferably amino.

Regardless of the radicals R1-R3And1And2and (X)nand preferably in combination with preferred meanings of one or more of these radicals are most preferred are the following values of R4:

R4is, for example, radical fo the mules In 3-D3and In3and D3preferably such, as defined below.

R4preferably is hydrogen, alkyl with 1-4 carbon atoms, phenyl or cycloalkyl with 3-6 carbon atoms, and each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms; or is formyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl; preferably hydrogen, stands, ethyl, n-propylene or isopropyl; most preferred is sustained fashion hydrogen.

Regardless of the radicals R1-R4And2and (X)nand preferably in combination with preferred meanings of one or more of these radicals are most preferred are the following values And1:

And1is a direct alkylene with 1-5 carbon atoms or a direct Alcanena or akinlana with 2-5 carbon atoms, and each of the three last named of diradicals unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, thiocyanato and the radical of the formula-B4-D4,

In4is a direct bond or divalent group of formula-O-, -SO2-, -CO-,-O-CO-, -NRo-, -NRo-CO-, -CO-NRo-, -O-CO-NRo- or-NRo-CO-O-, and

Roand D4independently are hydrogen, (C1-C4)alkyl with 1-4 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, MES is(C 1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms.

And1preferably is a radical of the formula-CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2- or-CH2CH2CH2CH2CH2-, which is unsubstituted. Also preferred is one of the above radicals, which is substituted one or more specified radicals-B4-D4. And1most preferably is a radical of the formula-CH2CH2- or-CH2CH2CH2-, which is unsubstituted or substituted by one or two radicals of hydroxy, alkyl with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms.

Regardless of the radicals R1-R4And1and (X)nand preferably in combination with preferred meanings of one or more of these radicals, the following values And2are Nai is more preferred:

And2preferably is a direct bond or a group of formula-CH2-, -CH2CH2-, -CH2CH2CH2- or-CH2CH2CH2CH2-, and each of the 4 last mentioned diradicals unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, thiocyanato and radicals of the formula-B5-D5or is divalentin the radical of the formula V1, V2, V3, V4or V5,

-CR6R7-W*CR8R9(V1)

-CR10R11-W*CR12R13-CR14R15(V2)

-CR16R17-CR18R19-W*CR20R21(V3)

-CR22R23-CR24R25-W* (V4)

-CR26R27-W* (V5)

moreover, each of the radicals R6-R27independently is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula-B6-D6, W is oxygen atom, sulfur or a group of the formula N(B7-D7and In5In6In7D5D6and D7such as defined below,

And2most preferably is a direct bond or a group of formula-CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2-O-CH2-, -CH2 2-CH2-, -CH2-CH2-O-CH2-, -CH2-S-CH2-, -CH2-S-CH2-CH2-, -CH2-CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-, -CH2-N(CH3)-CH2-, -CH2-N(CH3)-CH2-CH2- or-CH2-CH2-N(CH3)-CH2-.

In1In2In3and7preferably independently represent a direct bond or divalent group of formula-C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH - or-C(=Z*)-NR*-, where Z* is an oxygen atom or sulfur, Z** is an oxygen atom or sulfur and R* is an alkyl with 1-4 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)-alkoxy]CT is onila, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms;

also preferably1In2In3and7independently are a direct bond or divalent group of formula-C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH - or-C(=Z*)-NR*-, where Z* is an oxygen atom or sulfur, Z** is an oxygen atom or sulfur and R* is an alkyl with 1-4 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, formyl, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl and, in the case of cyclic radicals, Ala the La with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, preferably, R* = alkyl with 1-4 carbon atoms or cycloalkyl with 3-9 carbon atoms, or preferably R* = phenyl or phenyl-(C1-C4)alkyl, where each of the 2 last mentioned radicals in parts of phenyl unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms.

In4In5and6preferably independently represent a direct bond or divalent group of formula-O-, -S(O)p-, -S(O)p-O-. -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NRo-, -O-NRo-, -NRo-O-, -NRo-CO-, -CO-NRo-, -O-CO-NRo- or-NRo-CO-O-, and p is an integer 0, 1 or 2 and R° is hydrogen, alkyl with 1-4 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino is, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, and preferably Rois hydrogen, alkyl with 1-4 carbon atoms or cycloalkyl with 3-6 carbon atoms, or preferably R° is phenyl or phenyl-(C1-C4)alkyl, and each of the two last mentioned radicals in parts of phenyl unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms or haloalkoxy with 1-4 carbon atoms.

In4In5and6also preferably independently represent a direct bond or divalent group of formula-O-, -S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -NRo-, -NRo-CO-, -CO-NRo-, -O-CO-NRo- or-NRo-CO-O-, and p is an integer 0, 1 or 2, preferably 0 or 2, and Rothis, as stated above, most preferably is hydrogen or alkyl with 1-4 atom is mi of carbon.

D1D2D3D4D5and D6preferably independently are hydrogen, alkyl with 1-6 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 carbon atoms or (C3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, alkylsulfonyl with 1-4 carbon atoms and haloalkaliphilic with 1-4 carbon atoms and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms.

Also preferably D1D2D3D4D5and D6independently are alkyl with 1-4 carbon atoms, phenyl, phenyl-(C1-C4)alkyl, cycloalkyl with 3-6 the volumes of carbon or (C 3-C6)cycloalkyl-(C1-C4)alkyl, where each of the five last mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, formyl, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-9 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl and, in the case of cyclic radicals, alkyl with 1-4 carbon atoms and haloalkyl with 1-4 carbon atoms, and preferably is an alkyl with 1-4 carbon atoms or cycloalkyl with 3-6 carbon atoms or a phenyl or phenyl-alkyl with 1-4 carbon atoms, and each of the two last mentioned radicals in parts of phenyl unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms or haloalkoxy with 1-4 carbon atoms.

Regardless of the radicals R1-R4And1and2and preferably in combination with preferred meanings of one or more of these radicals are most preferred is vlahuta the following values (X) n:

(X)nrepresents n substituents X and X independently is halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, alkenyl with 2-4 carbon atoms, quinil with 2-4 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)alkylamino-carbonyl, N-(C1-C6)alkanolamine or N-(C1-C4)alkanoyl-N-(C1-C4)alkylamino,

each of 13 last mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-6 carbon atoms, (C3-C6)cycloalkyl-amino, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, aminocarbonyl, mono(C1-C4)alkylamino-carbonyl, di(C1-C4)-alkylamino-carbonyl, phenyl, phenoxy, FeNi is thio, phenylcarbinol, heterocyclyl, heterocyclic, heterocyclic, heterocyclisation, and each of the 8 last-mentioned radicals is unsubstituted or has one or more substituents from the group halogen, nitro, cyano, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, (C1-C4)alkyl-carbonyl and (C1-C4)alkoxy-carbonyl,

or is cycloalkyl with 3-9 carbon atoms, phenyl, phenoxy, phenylthio, phenylcarbinol, heterocyclyl, heterocyclic, heterocyclic or heterocyclisation,

each of the 9 last-mentioned substituents, unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkylthio with 1-4 carbon atoms, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, cycloalkyl with 3-6 carbon atoms, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, amino-carbonyl, mono(C1-C4)alkylamino-carbonyl and di(sub> 1-C4)alkylamino-carbonyl,

or two adjacent radicals X together are unfused cycle with 4-6 ring atoms, which is carboxyl or contains a ring heteroatoms from the group O, S and N and which is unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms and oxo,

n is 0, 1, 2 or 3, preferably 1 or 2.

(X)nalso preferably represents n substituents X and X independently is halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, alkyl with 1-4 carbon atoms, cyano (C1-C4)alkyl, alkoxy with 1-4 carbon atoms, (C1-C4)alkylamino, di[(C1-C4)alkyl]-amino, halo, (C1-C4)alkyl, hydroxy-alkyl with 1-4 carbon atoms, (C1-C4)alkoxy(C1-C4)alkyl, halo(C1-C4)alkoxy(C1-C4)alkyl, alkylthio with 1-4 carbon atoms, halo-alkylthio with 1-4 carbon atoms, alkenyl with 2-6 carbon atoms, haloalkyl with 2-6 carbon atoms, quinil with 2-6 carbon atoms, haloalkyl with 2-6 carbon atoms, (C1-With4)alkylamino-( C1-C4)alkyl, di-[(C1-C4)alkyl]-amino-(C1-With4)alkyl, (C3-C6)cyclooctylamino-(C1-C4)alkyl, cyclo-alkyl 3-9 the volumes of carbon heterocyclyl(C1-C4)alkyl with 3 to 9 ring members, and a cyclic group in the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals, preferably up to 3 radicals from the group of alkyl with 1-4 carbon atoms, halogen and cyano, or is phenyl, phenoxy, phenylcarbinol, phenylcarbinol-(C1-C4)alkyl, (C1-C4)alkoxy-carbonyl-(C1-C4)alkyl, (C1-C4)alkylamino-carbonyl-(C1-C4)alkyl, (C1-C4)alkyl-carbonyl, (C1-C4)alkoxy-carbonyl, aminocarbonyl, (C1-C4)alkylamino-carbonyl, phenoxy-(C1-C4)alkyl, phenyl-(C1-C4)alkyl, heterocyclyl, heterocyclisation, heterocyclics, heterocyclic or one of 16 last mentioned radicals, which in the acyclic part or, preferably, in the cyclic part substituted by one or more radicals from the group halogen, nitro, cyano, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkoxy with 1-4 carbon atoms, formyl, (C1-C4)alkyl-carbonyl, (C1-C4)alkoxy-carbonyl, and these radicals heterocyclyl contains 3 to 9 ring atoms and 1-3 ring heteroatoms from the group N, O and S,or

two adjacent radicals X together are unfused cycle with 4-6 ring atoms, which is carbocyclic or contains a ring heteroatoms from the group O, S and N and which is unsubstituted or substituted by one or more radicals from the group halogen, alkyl with 1-4 carbon atoms, and oxo.

(X)nmost preferably represents n substituents X and X independently is halogen, HE, NO2, CN, SCN, alkyl with 1-6 carbon atoms, alkoxy with 1-6 carbon atoms, (C1-C4)alkylcarboxylic or (C1-C4)alkoxycarbonyl, and the 4 last mentioned radicals is unsubstituted or substituted with halogen or alkoxy with 1-4 carbon atoms, and

most preferably represents n substituents X and X independently is halogen, hydroxy, alkyl with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms.

In the above or the following radicals heterocyclyl independently is preferably a heterocyclic radical having 3-7 ring atoms and 1-3 heteroatoms from the group N, O and S, preferably a heteroaromatic radical from the group of pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, teinila, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furil, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, or is partially or completely is using gidrirovanny heterocyclic radical from the group of oxiranyl, oxetanyl, oxolane (=tetrahydrofuryl), oxania, pyrrolidyl, piperidyl, piperazinil, DIOXOLANYL, oxazolyl, isoxazolyl, oxazolidinyl, isoxazolidine and morpholinyl. Heterocyclyl most preferred is a heterocyclic radical with 3-6 ring atoms and one heteroatom from the group N, O and S, preferably heteroaromatic radical with 5 or 6 ring atoms or a saturated or partially unsaturated heterocyclic (not heteroaromatic) radical with 3-6 ring atoms.

In addition, heterocyclyl is preferably a heterocyclic radical with 5 or 6 ring atoms and 2 or 3 heteroatoms from the group N, O and S, preferably pyrimidinium, pyridazinyl, pyrazinium, triazinium, thiazolium, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, triazolyl or piperazinil, DIOXOLANYL, oxazolidines, isoxazolyl, oxazolidinyl, isoxazolidine or morpholinium.

The number of carbon atoms of the sum of the carbon atoms of both radicals And1and A2-R2preferably is:

a) at least 6 carbon atoms, preferably 6-20 carbon atoms, most preferably 6 to 12 carbon atoms, or

b) 5 carbon atoms, and in this case, And1is a group of the formula the CH 2- or-CH2CH2-, a R1is an alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms, haloalkyl with 2-6 carbon atoms or cycloalkyl with 3-9 carbon atoms, which is unsubstituted or substituted, preferably R1is an alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms or cycloalkyl with 3-6 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group of alkyl with 1-4 carbon atoms.

The total number of carbon atoms in the radicals And1and A2R2preferred alternative specified option a).

This group-A2-R2preferably is cyclopropyl (- RG), CH2- - RG, -(CH2)2with WG, cyclobutyl (“Vie”), CH2-VI, -(CH2)2with VI, oxiranyl, oxiranyl-stands or 2-(oxiranyl)-et-1-yl.

The subject of the proposed invention is also a method of obtaining compounds of General formula (I) or their salts, characterized in that

a) compound of formula (II)

R1-Fu (II)

where Fu is a functional group from the group of ester carboxylic acids, complex orthoevra carboxylic acid, carboxylic acid chloride, carboxylic acid amide, carboxylic acid anhydride and trihalomethyl,

subjected to interaction with the compound of the formula (II) or its salt, formed by the addition of acid,

or b) the compound of formula (IV)

where Z1is a radical capable of currency, or side group, for example chlorine, trichloromethyl, alkylsulfonyl with 1-4 carbon atoms and unsubstituted or substituted phenyl-( C1-C4)alkylsulfonyl or (C1-C4)alkylphenolethoxylate, is subjected to the interaction with a suitable amine of formula (V) or its salt formed by the addition of acid,

moreover, in formulas (II), (III), (IV) and (V) radicals R1, R2, R3, R4, A1And2and X and n are the same as in the formula (I).

The interaction of compounds of the formula (II) and (III) is carried out preferably by means of catalysis by bases in an inert organic solvent, for example tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methanol and ethanol, at temperatures between -10°and the boiling point of the used solvent, preferably at a temperature of 20-60°With; in the case of salts formed by the addition of acid, of the formula (III), usually spend their selection with base in situ. As bases or basic catalysts are suitable hydroxides, Melo and, hydrides of alkali, alkali carbonates, alkali alcoholate, hydroxides of alkaline earth metals, hydrides of alkaline earth metals, carbonates of alkaline earth metals or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. The amount used of the base is, for example, in the limit of 0.1 to 3 molar equivalents relative to the compound of formula (III). The compound of formula (II) can be used, for example, in equimolar ratio or excess to 2 molar equivalents to the compound of formula (III). Corresponding methods are described in more detail in the existing literature (see Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3; Part 2B; ISBN 0-08-030703-5, S. 290).

The conversion of compounds of formulas (IV) and (V) is carried out preferably by means of catalysis by bases in an inert organic solvent, for example tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methanol and ethanol, at temperatures between -10°and the boiling point of the used solvent, preferably at a temperature of 20-60°C; and in the case of the compounds of formula (V) in the form of a salt formed by the addition of acid, as a rule, hold his selection with base in situ. As bases or basic catalysts suitable are the alkali hydroxides, Hydra the water alkaline, the alkali carbonates, alkali alcoholate, hydroxides of alkaline earth metals, hydrides of alkaline earth metals, carbonates of alkaline earth metals or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. The amount used of the base is, for example, in the limit of 1-3 molar equivalents relative to the compound of formula (IV). The compound of formula (IV) can be used in equimolar ratio or excess to 2 molar equivalents to the compound of formula (V). Corresponding methods are described in more detail in the existing literature (see Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol. 3; Part 2B; ISBN 0-08-030703-5, S. 482).

Educti formula (II), (III), (IV) and (V) are either commercially available or can be obtained according to or analogously to the methods described in known literature. Individual compounds of formulas (III) and (V) are new and are the subject of this invention. These compounds can also be obtained, for example, one of the following described methods.

The compound of formula (IV) or its immediate preliminary stage receive, for example, in the following way:

1. By reacting the compounds of formula (II) with a derivative amidino-thiourea of the formula (VI)

where Z2is (C1-C4-alkyl or phenyl-(C 1-C4)-alkyl, and R3the same as in the formula (I),

get the compounds of formula (IV)in which Z1=-SZ2.

2. By the interaction of amidine formula (VII) or its salt formed by the addition of acid,

H2N-CR1=NH (VII)

where R1the same as in the formula (I),

N-cyanodithioiminocarbonate formula (VIII),

NC-N=C(S-Z3)2(VIII)

where Z3is an alkyl with 1-4 carbon atoms or phenyl-(C1-C4)-alkyl,

get the compounds of formula (IV), where Z1=-S-Z2.

3. Through the cooperation of dicyanamide alkali derived from carboxylic acids mentioned formula (II) obtain the compounds of formula (IV), where

Z1=NH2.

4. Through the cooperation of trichloroacetonitrile with a nitrile of the formula (IX),

R1- (CN IX),

where R1the same as in the formula (I),

first get the compounds of formula (X)

where Z1and Z4are CCL3,

then turn with compounds of the formula H-R3(R3the same as in the formula (I)) to obtain compounds of the formula (IV), where Z1=CCl3.

The transformation of the carboxylic acid derivatives of the formula (II) derivative amidino-thiourea of the formula (VI) is carried out preferably by means of catalysis by bases in an organic solvent, neprimerene, tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, methanol and ethanol, at temperatures between -10°and the boiling point of the used solvent, preferably at a temperature of 0-20°C. the conduct of interaction is possible in water or in aqueous mixtures of solvents with one or more of the above organic solvents. In the case of the compounds of formula (IV) in the form of a salt formed by the addition of acid, it may be the selection with the base in situ. As bases or basic catalysts suitable are the alkali hydroxides, hydrides of alkali, alkali carbonates, alkali alcoholate, hydroxides of alkaline earth metals, hydrides of alkaline earth metals, carbonates of alkaline earth metals or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. The amount used of the base is, for example, in the limit of 1-3 molar equivalents relative to the compound of formula (VI). Compounds of formulas (II) and (VI) can be used in equimolar ratio or excess to 2 molar equivalents to the compound of formula (II). Corresponding methods are described in more detail in the existing literature (see N. Eilingsfeld, H.Scheuermann, Chem. Ber.; 1967, 100, 1874), the corresponding intermediates of formula (IV) are new.

Maintains deistvie amidino formula (VII) with N-cyanodithioiminocarbonate formula (VIII) is carried out preferably by means of catalysis by bases in an inert organic solvent, for example acetonitrile, dimethylformamide, dimethylacetamide, N-organic, methanol and ethanol, at temperatures between -10°and the boiling point of the used solvent, preferably at a temperature of 20-80°C. In the case of the compounds of formula (VII) in the form of a salt formed by the addition of acid, it may be the selection with the base in situ. As bases or basic catalysts suitable are the alkali hydroxides, hydrides of alkali, alkali carbonates, alkali alcoholate, hydroxides of alkaline earth metals, hydrides of alkaline earth metals, carbonates of alkaline earth metals or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene. The amount used of the base is, for example, in the limit of 1-3 molar equivalents relative to the compound of formula (VIII). Compounds of formulas (VII) and (VIII) can be used in equimolar ratio or in excess of 2 molar equivalents to the compound of formula (VII). Corresponding methods are described in more detail in the existing literature (see T.A. Riley, W.J. Henney, N.K. Dalley, B.E. Wilson, R.K. Robins; J. Heterocyclic Chem.; 1986, 23(6), 1706-1714), the corresponding intermediates of formula (IV) are new.

The intermediate products of the formula (X), where Z’ is chlorine, possibly by interacting with titianum is Yes alkaline, with a carboxylic acid derivative of the formula (II), and in this case Fu is preferably a functional group of carboxylic acid chloride or carboxylic acid amide. The conversion of the reaction components is carried out, for example by acid catalysis in an inert organic solvent, for example toluene, chlorobenzene, chlorinated hydrocarbons, at temperatures between -10°and the boiling point of the used solvent, preferably at a temperature of 20-80°and perhaps the chlorination of the intermediate products obtained in situ using a suitable chlorination reagent such as phosphoroxychloride. Suitable acids are, for example, halogen acids, such as Hcl, or a Lewis acid, for example, ll3or F3(see U.S. patent And 5095113, Du Pont).

The intermediate products of the formula (X), where Z’, Z4are three-halogenmethyl, possibly by interaction of the corresponding NITRILES trigalogenmetany acid nitrile carboxylic acid of formula (IX). The conversion of the reaction components is preferably carried out by means of acid catalysis in an inert organic solvent, for example toluene, chlorobenzene, chlorinated hydrocarbons, at temperatures between -40°and the boiling point of the used solvent, preferably at a temperature of from -10 to 30°C. Approach is asimi acids are, for example, halogen acids, such as Hcl, or a Lewis acid, for example, ll3or F3(see European patent A-130939, Ciba Geigy).

Intermediates of formula (IV), where Z1is (C1-C4)allylmercaptan or unsubstituted phenyl-(C1-C4)allylmercaptan, is subjected to the interaction in an inert organic solvent, for example toluene, chlorobenzene, chlorinated hydrocarbons, etc. at a temperature between -40°and the boiling point of the used solvent, preferably at a temperature of 20-80°With a suitable reagent chlorination, for example ordinary chlorine or phosphoroxychloride, to get capable to transform chlorotriazine formula (IV), where Z1is chlorine (see J.K. Chakrabarti, D.E. Tupper; Tetrahedron 1975, 31(16). 1879-1882).

Intermediates of formula (IV), where Z1is (C1-C4)allylmercaptan or unsubstituted or substituted phenyl-(C1-C4)allylmercaptan or (C1-C4)alkalinity, can be subjected to oxidation in an inert organic solvent, such as chlorinated hydrocarbons, acetic acid, water, alcohols, acetone or their mixtures, at a temperature between 0°and the boiling point of the used solvent, preferably at a temperature of 20-80°With a suitable reagent oxidation, e.g. the measures m-chloroperbenzoic acid, hydrogen peroxide, peroxomonosulfate potassium (see T.A. Riley, W.J. Henney, N.K. Dalley, B.E. Wilson, R.K. Robins; J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714).

To obtain the salts of the compounds of formula (I)formed by the addition of acid, use the following acid: halogen acids, for example hydrochloric acid or Hydrobromic acid, another phosphoric acid, nitric acid, sulfuric acid, mono - or bifunctional carboxylic acids and hydroxycarbonate acid, for example acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and sulphonic acids, for example p-toluensulfonate acid or 1,5-naphthalenedisulfonic acid. The compounds of formula (I)formed by the addition of acid can be obtained in a simple way by the usual methods of education salts, for example the compounds of formula (I) is dissolved in a suitable organic solvent, for example methanol, acetone, methylene chloride or gasoline, and then spend the accession acid at a temperature of 0-100°and allocate a known manner, for example by filtration, and, in this case, purified with the aid of an inert organic solvent by washing.

Obtaining salts of compounds of formula (I), obrazu what's the connection of the bases, carried out preferably in an inert organic solvent, for example water, methanol or acetone, at a temperature of 0-100°C. Suitable bases for obtaining suggested salts are, for example, alkali carbonates such as potassium carbonate, hydroxides of alkali and alkaline earth metals, such as NaOH or KOH, hydrides of alkali and alkaline earth metals, for example NaH, the alcoholate of alkali and alkaline earth metals, for example methanolic sodium tertiary butyrate, potassium, or ammonia or ethanolamine. Quaternary ammonium salts can be obtained, for example, by reacting or condensing with Quaternary ammonium salts of fomula [NRR'R’R’’]+X-where R, R’, R’ and R’’ independently are alkyl with 1-4 carbon atoms, phenyl or benzyl, and X-is an anion, for example CL-or HE-.

By “inert solvent”specified in the proposed implementation of the proposed method, see solvent which is inert under reaction conditions. However, this solvent should be inert under any reaction conditions.

The proposed compounds of formula (I) and their salts, hereinafter referred to as the (proposed) the compounds of formula (I)demonstrate excellent herbicide activity against a wide spectrum of economic is important weeds of the families of monocots and dicots. Also the active substances are suitable for combating perennial weeds. It does not matter how the introduction of the proposed substance: before sowing, before you shoot or post-emergent plants.

In particular, for example, is called a separate species of flora weeds families of monocots and dicots, which can be controlled through the use of the proposed connection without restrictions on certain types.

Weeds of the family of monocots are, for example, oats, chaff, Alopecurus, reed Canary grass, barnyard grass, weed, spickle, as well as certain types of site; perennial monocotyledonous species in the family are, for example, wheat grass, cynodon and sorghum, and certain types of site. In dicotyledonous weed grasses range of actions proposed compounds extends to species such as, for example, Galium, viola, Veronica, dead-nettle, starwort, amaranth, mustard, ipomea, Matricaria, abutilon and SIDA, as well as perennial species, such as bindweed, Thistle, sorrel and tarragon. Also suggested that the active substances are effective against weeds, breeding shoots in specific conditions, such as arrowheads, Alisma, bolotnitsa, Kamashi and syt.

The proposed connection is applied to the surface before emergence of the plants, thus to seal the cut sprouts sprouts of weeds, or the weeds grow to the stage of emergence of leaves, but then their growth stops and they completely disappear in 3-4 weeks.

When applying the active compounds in green parts of plants after germination also occurs very quickly characterized by cessation of growth, and weed plants stop at the stage of growth at the time of processing or die after a certain time, so the weeds that are harmful to cultivated plants, is eliminated at a very early stage and for a long time.

Also proposed compounds demonstrate excellent herbicide activity against monocotyledonous and dicotyledonous weeds, but do not have much influence or are completely harmless for cultivated plants, economically important, for example wheat, rye, rice, maize, sugar beet, cotton and soya. Thus, the proposed compounds are suitable for the selective combating the growth of unwanted plants in agricultural and ornamental crops.

In addition, the proposed substance exhibit excellent properties that regulate the growth of cultivated plants. They regulate the metabolism of plants and can have an impact on the balance of substances of plants and increased productivity. In addition, proposed the e substances are also suitable for primary control and deceleration unwanted vegetative growth without dying plants. Slow vegetative growth plays an important role in monocotyledonous and dicotyledonous crops, as a result, it is possible to reduce or completely reduce the exposure time.

The active substance on the basis of their herbicide and regulating the growth of plants properties can also be used for combating harmful plants in known or even changing due gennoinzhenernuju development cultures. Transgenic plants have, as a rule, the most preferred properties, such as resistance to known pesticides, primarily known to herbicides, resistance to plant diseases or pathogens of plant diseases, such as fungi, bacteria or viruses.

Other special properties are, for example, to obtain a certain amount of yield, quality, storage stability, the composition and special ingredients. Thus becoming known transgenic plants with increased force or modified as forces or other fatty acid composition.

Preferred is the use of the proposed compounds of formula (I) or their salts in technical and decorative transgenic crops of economic significance, such as wheat, barley, rye, oats, millet, rice and maize, and sugar beet, cotton, soybean, rape, potatoes, tomatoes, peas and other vegetables. The compounds of formula (I) preferably used as herbicides in commercial crops, which are resistant, or who make persistent in the genetic engineering changes to any phototoxic action of herbicides.

Traditional methods of obtaining new plants, compared to the so far obtained cultures have modified properties are, for example, in the classical methods of cultivation and obtaining mutants. Alternatively you can obtain new crops with modified properties when using genetic engineering methods (see European patent EP-A-0221044, European patent EP-A-0131624). For example, describe a few possible options

- genetically engineered changes in technical plants in order to modify the synthesizing force (see international application WO 92/11376, international application WO 92/14827, international application WO 91/19806).

transgenic crop plants which are resistant to known herbicides, type glufosinate (see European patent EP-A-0242236, European patent EP-A-242246) or glyphosate (international application WO 92/00377) or sulfonylurea (European patent EP-A-0257993, the U.S. patent And 5013659).

transgenic crop plants, for example cotton, with the ability to receive Bacillusthuringiensis-Toxine (Bt toxins), which contribute to the resistance of plants to certain pests (European patent EP-A-0142924. European patent EP-A-0193259).

transgenic plants with modified composition of fatty acids (international application WO 91/13972).

Numerous molecular biology techniques, using which it is possible to obtain transgenic plants with modified properties, in principle, are known; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2 Aufl. Cold Spring Harbor Laboratory Press, Gold Spring Harbor, NY; or Winnacker “Gene und Klone”, VCH Weinheim 2. Edition 1996 or Christou, Trends in Plant Science” 1 (1996), 423-431).

When carrying out genetic engineering technologies such possible introduction of a molecule of nucleic acid in the plasmid, which promote mutagenesis or consistent change by recombination of DNA sequences. When you use these basic methods is possible, for example, replacement of the grounds, the removal of part of the sequence or the addition of natural or synthetic sequences. To join DNA fragments with each other can be used adapters or linkers.

Obtaining plant cells with a reduced activity of a gene product is carried out by the expression of at least one antisense RNA, one sense RNA to obtain compressionquality or expression, at least one of the corresponding ribozyme, which separates the specific transcript of the abovementioned gene product.

Moreover, it is possible to use DNA molecules, which contain the entire coding sequence of the gene product, including possible existing flanking sequences, and the use of DNA molecules that contain only parts of the coding sequence, and these parts must be long enough to activate the antisense effect in the cells. Also is it possible to use DNA sequences that have a high degree of homogeneity with the coding sequences of the gene product, however, are not completely identical.

When the expression of nucleic acid molecules in plants possible localization of the synthesized protein in a specific part of the plant cell. To obtain localization in a certain part may, for example, the connection coding region sequences of DNA that contribute to localization in a certain part. Such sequences are known to the person skilled in the art (for example, see Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et. al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et. al., Plant J. 1 (1991), 95-106).

Trangene plant cells can be regenerated by known methods is to whole plants. And we are talking about any kind of transgenic plants, i.e. as monocots and dicots.

Thus, the gain of transgenic plants which have modified properties due to irexpress, suppression or inhibition of homologous (natural) genes or gene sequences or expression of heterologous (foreign) genes or gene sequences.

Preferably the proposed compounds of formula (I) can be used in transgenic crops which are resistant to herbicides from the group of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances.

In addition to effective actions proposed active substances against weeds in transgenic crops, in other cultures also see optimal actions with the proposed active substances, for example the fight with a modified or specifically an expanded spectrum of weed grasses, the change in the amount of consumption of the proposed active substances, preferably good combinability with the herbicides to which are resistant transgenic crops and the impact on growth and yield of transgenic crops.

Therefore, the object of the proposed invention is also the use of the proposed compounds (I) as g is of Ruzinov to fight against harmful plants in transgenic cultivated plants.

The proposed use for combating harmful plants or for regulating the growth of plants, in which the active substance of the formula (I) or its salt before application to plants, the plants or the soil is formed from the primary substance (Prosobranchia).

The proposed compounds may be used in the form of a sprayable powders, emulsifying concentrates, spray solutions, their agents or granular products in a normal ready form. Therefore, the subject of this invention is also herbicide and regulating plant growth agent, which contain compounds of the formula (I).

The compounds of formula (I) can be represented in different forms, depending on the biological and/or chemico-physical parameters.

Possible forms are, for example, spray powder, water soluble powder, water soluble concentrates, emulsifying concentrates, emulsions, such as oil-in-water” and “water in oil”spray solutions, suspension concentrates, dispersions on an oil or water-based, mixed with oil solutions, suspensions, capsules, pollinating agent, agent for etching, granular products for application by spraying or by introduction into the soil, granular products in the form of finely granulated products, granulares the installed products for spraying, adsorption granular products, dispersible in water, granulated products, water-soluble granular products, ultraviolet shape, microcapsules and waxes.

These separate kinds of forms, in principle, are known and described, for example, in Winnacker-Kuchler, “Chemische Technologie”, Band 7, C. Hauser Verlag Munchen, 4. Aufl. 1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

Necessary additives for making preparative forms, such as inert materials, surfactants, solvents and other additives are also known and described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N. J., H.v.; Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutchen''s “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzflachenaktive Athylenoxidad-dukte”, Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, “Chemische Technologie”, Band 7, C. Hauser Verlag Munchen, 4. Aufl. 1986.

On the basis of these forms are available for combinations with other substances, acting as pesticides, for example insecticides, herbicides, fungicides, and fertilizers and/or growth regulators, for example, in the form of a ready form or by mixing in the tank.

Sprayable powders are preparations evenly despergiruemaya water, which, together with the active substance, with the exception of a diluent or inert substance, also contain additional Jonnie and/or nonionic surfactants (wetting agent, dispersing agent, for example polyoxyethylene ALKYLPHENOLS, polyoxethylene fatty alcohols, polyoxyalkylene fatty amines, polyglycolether fatty alcohols, alkanesulfonyl, alkylbenzenesulfonate, lignin sulfonate sodium 2,2’-dynafilter-6,6’-disulfonate sodium, dibutylaminoethanol sodium or sodium railneteurope acid. To obtain a sprayable powders herbicide active substances are crushed, for example, in a conventional apparatus such as hammer mills, pneumatic mills and vozduhonosnykh mills, and simultaneously or immediately after mixed with additives to obtain the form.

Emulsifying concentrates are obtained by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or high-boiling aromatic hydrocarbons or operatorto, or mixtures of organic solvents with one or more ionic and/or nonionic surfactants (emulsifiers). As emulsifiers can, for example, use: calcium salts alkylarylsulfonate the Oh of the acid, for example dodecylbenzenesulfonate calcium, or nonionic emulsifiers, for example, a complex polyglycolic ether fatty acids, simple alkylarylsulphonates ether, simple polyglycolic ether fatty acids, the condensation products of propylene oxide and ethylene oxide, simple alkylpyridine, complex sorbitolovy ethers, for example a complex ester polyoxyethylenesorbitan fatty acids.

Pollinating agent is obtained by grinding the active substance with finely distributed solid substances, for example talc, natural clays, such as bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water or oil based. They can be obtained, for example, by grinding uverennogo of material by means of commercially available bead mills and, in this case, with the addition of surface-active substances, such as, for example, that described above for other types of forms.

Emulsions, for example oil-in-water” receive, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, in this case, surface-active substances, such as, for example, that described above for other types of forms.

Granular products can be obtained or by foaming the active substances capable of adsorbirovanny, granulated inert material or by applying concentrates of active substances by using an adhesive agent, for example polyvinyl alcohol, sodium polyacrylate or mineral oils on the surface of the carrier, such as sand, kaolinites or of inert material. Also surfactants can be granulated in the usual way of producing granulated products fertilizers, preferably when mixed with fertilizer.

Granular products, dispersible in water, receive, as a rule, in the usual way as, for example, spray drying, granulation in the vortex layer, graining on the plate, mixing with high-speed mixers and extrusion without the use of solid inert materials. To obtain a granulated product on the plate in the fluidized bed, extruder and spray dryer, see, e.g., “Spray-Drying Handbook”, 3rd ed. 1979, G. Goodwin Ltd. London; J.E.Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer''s Handbook", 5th Ed" McGraw-Hill, New York 1973. S. 8-57.

Other details of the compilation of the forms of agents for plant protection are described, for example, in G.C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 and J.D. Freyer, S.A. Ewans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publicationc, Oxford, 1968, Seiten 101-103.

Agrochemical forms contain as a rule 0.1 to 99 wt. -%, preferably 0.1 to 95% of the mass. active substances is tion of the formula (I). The concentration of active substance in spray powders is, for example, about 10-90% of the mass. radical, made of 100% of the usual components of the form. The concentration of active substance in emulsifying concentrates may be about 1-90, preferably 5-80 wt%. Powdered formulation containing 1-30 wt%. the active substance, preferably at least 5-20% of the mass. the active substance. Spray solutions contain about 0.05 to 80, preferably 2-50% of the mass. the active substance. Granular products, dispersible in water, the active substance depends, in solid or liquid state is proposed active connection, and what use granular additives, fillers and others. Granular products, dispersible in water, the active substance is, for example, 1-95, preferably 10-80% of the mass.

In addition, these forms of active substances, in this case, contain conventional adhesive agents, wetting agents, dispersing agents, emulsifying agents, penetrating agents, stabilizing agents, marathonissi agents and solvents, fillers, carriers and colorants, antispyware, evaporation inhibitors and agents that affect the pH and viscosity.

As a matching partner for PR is glorennec active substances in mixed form or mixed in the tank is used, for example, a known substance, which are described, for example, in Weed Research 26, 441-445 (1986), or in “The Pesticide Manual”, 10th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry, 1994 and are there links. Known from literature herbicides which can be combined with compounds of formula (I)are the following active substances (note: connections give under “common names” according to the international organization for standardization (ISO) or under chemical names, in this case, with the usual code number): acetochlor; alfthan; AKN 7088, that is, [[[1-[5-[2-chloro-4-(trifloromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyaniline]-amino]-oxy]-acetic acid and methyl ester [[[1-[5-[2-chloro-4-(trifloromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyacridine]-amino]-oxy]-acetic acid; alachlor; aloxide; ametrine is high; amidosulfuron; amitrole; AMS, i.e. sulpham ammonium; anilofos; Azul; atrazine; azimsulfuron (DPX-A8947); isoprotein; Barban; BAS 516 N, i.e., 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one; benzoin; benfluralin; beforethat; benzylbromide; bensulide; bentazon; benzien; bentover; benzoylperoxy-ethyl; benzthiazole; bialaphos; bifenox; bromacil; bromobutyl; bromophenoxy; bromoxynil; brauron; buminate; butoxide; butachlor; butamifos; buenaflor; mutilatory; butalin; butyl; cafestol (SN-900); the carb is amide; Capistrano (ICI-A0051); CDAA, i.e. the 2-chloro-N,N-di-2-propylacetamide; CDEC, i.e. a complex 2-korallovy ether diethyldithiocarbamic acid; chlorethoxyfos; chloramben; lorazepam-butyl, chlormezanone (ICI-A0051); chlorbromuron; chlorbutol; chlorgenic; chlorofluro-methyl; ozone chloride; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorine; cinmetacin; chinaculture; clethodim; clodinafop and derived its esters (for example, clodinafop-propargyl); clomazone; clomipram; chloroxygen; clopyralid; cumyluron (JC 940); cyanazine; cycloate; cycloaliphatic (AC 104); cycloxydim; cyclotron; cyhalofop and derived its esters (for example, a complex butyl ether, DEH-112); supercoat; ziprin; cobresol; dameron; 2,4-DB; dalapon; desmedipham; desmetryn; di-Allat; dicamba; dichlobenil; dichlorprop; diclofop and their esters, for example diclofop-methyl; diacetyl; Difenoxin; difenzoquat; diflufenican; dimefuron; dimethachlor; deltamethrin; dimethenamid (SAN-582H); deltasone; clomazone; dimethipin; demetracopoulos; dinitramine; dinoseb; dinoterb; diphenamid; DIPROPYLENE; Diquat; dithiopyr; Diuron; DNOC; Eglinton-ethyl; EL 77, that is 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide; endothal; ARTS; asbroker; ethalfluralin; atomiculture-methyl; tidiman; idiosyn; Ecopolis is you; F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-forproper)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-econsultant; idoxifene and its esters (for example, a complex ethyl ester, HN-252); etamesonic (HW 52); fenoprop; phenoxy; fenoxaprop and fenoxaprop-P and its esters, for example fluazifop-butyl and fluazifop-P-butyl; fluchloralin; flumetsulam; flumeturon; flumiclorac and its esters (for example, complex pentalogy ether, S-23031); flumioxazin (S-482); flubiprofen; flupoxam (KNW-739); foregiven; foreglimpse-ethyl; flypaper (UBIC-4243); fluridone; fluro-chloride; fluroxypyr; flurtamone; fomesafen; fosamine; voreloxin; glufosinate; glyphosate; galasoft; halosulfuron and its esters (e.g. methyl ester, NC-319); haloxyfop and its esters; haloxyfop-R (R-haloxyfop) and its esters; hexazinone; imazamethabenz-methyl; imazapyr; imazaquin and salt, for example ammonium salt; imazethapyr; imazethapyr; imazosulfuron; ioxynil; isosorbid; isopropylene; Isoproturon; Sauron; isoxaben; isocaporate; carbocylic; lactofen; lentil; linuron; MSRA; SRV; mecoprop; mefenacet; mefluidide; metamitron; metazachlor; methabenzthiazuron; methamphetamine; metasol; methoxyphenol; methyldibromo; metaventure; metaventure; metobromuron; metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MN; molinet; monolid; monocarb the foreign dihydrophosphate; monolinuron; monuron; MT 128, that is 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinone; MT 5950, i.e., N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentane; nitroanilide; napropamide; naptalam; NC 310, that is, 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxyethanol; neburon; nicosulfuron; snipercraft; nicraly; nitrofen; nitrophorin; norflurazon; arrancars; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxycontin; a pair of quot; Babolat; pendimethalin; PERFLUORO; fenazepam; phenmedipham; picloram; piperophos; peribuccal; pirivena-butyl; pretilachlor; primisulfuron-methyl; procesin; prodiamine; propleuron; progenitin-ethyl; prometon; prometryn; propachlor; propanil; propaquizafop and its esters; propazine; profam; propisochlor; propyzamide; prosulfuron; prosulfocarb; prosulfuron (CGA 152005); panahar; pyrazoline; person; pyrazosulfuron-ethyl; paradoxien; peridot; pyrithiobac (KIH-2031); pyrexia and its esters (for example, a complex propargilovyh ether); quinclorac; quinmerac; CWinApp and proizvodnye its esters; quizalofop and quizalofop-R and proizvodnye their esters, for example quizalofop-ethyl; quizalofop-P-tefuryl and quizalofop-P-ethyl; renature; rimsulfuron (DPX-E 9636); S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propenyloxy)-phenyl]-4,5,6,7-tetrahydro-2H-indazol; sebumeter; sethoxydim; sibron; Simazine; simetryn; SN 106279, i.e. 2-[[7-[2-x is the PR-4-(trifter-methyl)-phenoxy]-2-naphthalenyl]-oxy]-propanoic acid methyl ester 2-[[7-[2-chloro-4-(trifter-methyl)-phenoxy]-2-naphthalenyl]-oxy]-propanoic acid; sulfentrazone (FMC-97285, F-6285); colfuturo; sulfometuron-methyl; sulfosate (ICI-A0224); TCA; tabulam (GCP-5544); tebuthiuron; terbacil; thermocarb; turbuhaler; terbumeton; terbutylazine; terbutryn; TFH 450, i.e., N,N-diethyl-3-[(2-ethyl-6-were-sulfonyl]-1H-1,2,4-triazole-1-carboxamide; tanishlar (NSK-850); diazafluoren; thisour (Mos-13200); thidiazuron (SN-24085); thifensulfuron-methyl; thiobencarb; thiocarbonyl; tralkoxydim; three-Allat; triasulfuron; threatened; tribenuron-methyl; triclopyr; tridiphane; triazine; trifluralin; triflusulfuron and its esters (e.g. methyl ester, DPX-66037); timetron; dicode; vernolate; WL 110547, that is, 5-phenoxy-1-[3-(trifluoromethyl)-phenyl]-1H-tetrazol; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MVN-001; KIH-9201; ET-751; KIH-6127 and KIH-2023.

When using commercially available form in the usual way diluted with water, for example, when applying sprayable powders, emulsifying concentrates, dispersions and granular products, dispersible in water. Powder form, granular products for spraying or injection into the soil, and spray solutions before use, usually slightly diluted with other inert substances. The flow rate of the compounds of formula (I) varies depending on external conditions, such as temperature, humidity, the type and the use of herbicides and others. The flow rate of the active substance may be, for example, from 0.01 to 10.0 kg/ha or more, preferably 0.05 to 5 kg/ha

In the following examples, the link is on quantitative data (percentage data), because specially are not specified.

A. Chemical examples

Example A1

2-Amino-4-(1-fluoro-1-methyl-ethyl)-6-(3-phenyl-1-cyclobutyl-1 propylamino)-1,3,5-triazine (see table 4, example 4-2)

To 1,90 g (0,00613 mol) of 3-phenyl-1-cyclobutyl-1-(biguanidine)-propane hydrochloride in 30 ml of methanol and 2 g of molecular sieve 3 Angstrom add a solution obtained from 0,32 (0.014 mol) of sodium and 10 ml of methanol. To the mixture are added dropwise 1.10 g (0,0092 mol) of a compound methyl ester 1-fluoro-1-methyl-propionic acid and then stirred for 2 hours at a temperature of 25°and for 4 hours at a temperature of 65°C. the Reaction mixture is filtered, the filtrate concentrated and the residue is absorbed in a complex acetic ether. The mixture is then washed with water and dried using sodium sulfate. The desiccant is removed and the solvent is evaporated in vacuum. After purification via chromatography on a column (solvent: complex ethyl ester of acetic acid) to obtain 1.66 g (79% of theory) of 2-amino-4-(1-fluoro-1-methyl-ethyl)-6-(3-phenyl-1-cyclobutyl-1 propylamino)-1,3,5-triazine.

Example A2

2-Amino-4-(1-fluoro-1-methyl-ethyl)-6-(1-phenyl-4-cyclobutyl-4-butylamino)-1,3,5-triazine (see example 22-12, that the person 22)

1.52 g (0,008 mol) 2-amino-4-chloro-6-(1-fluoro-1-methyl-ethyl)-1,3,5-triazine and 1.64 g (0.012 mol) of calcium carbonate are placed in 30 ml of acetonitrile. To this solution are added dropwise 1.50 g (0,008 mol) of 4-phenyl-1-cyclopropyl-1 butanamine dissolved in 10 ml of acetonitrile. Then the solution is boiled for 3 hours on the phlegm. Then the solid components were removed and the filtrate is passed through a centrifuge. The residue is purified via chromatography on a column (solvent: methyl ester of acetic acid). Get a 2.36 g (86% of theory) of 2-amino-4-(1-fluoro-1-methyl-ethyl)-6-(1-phenyl-4-cyclobutyl-4-butylamino)-1,3,5-triazine.

Example A3

2-Amino-4-(fluoro-1-methyl-ethyl)-6-[3-(3, 5dimethylphenyl)-1-cyclobutyl-1 propylamino]-1,3,5-triazine (see table 9, example 9-17)

To 8,1 g (0,025 mol) of 3-(3, 5dimethylphenyl)-1-cyclopropyl-1-(biguanidine)-propane hydrochloride in 50 ml of methanol and 7 g of crushed molecular sieves 3 Angstrom add a solution of methanol obtained from 1.2 g (0.05 mol) of sodium and 100 ml of methanol. To the mixture are added dropwise to 5.4 g (0.045 mol) of a compound methyl ester 1-fluoro-1-methyl-propionic acid, and then stirred for 2 hours at a temperature of 25°and for 4 hours at a temperature of 65°C. the Reaction mixture is filtered, the filtrate concentrated and the residue is absorbed in a complex acetic ether. The mixture is then washed with water and dried using sodium sulfate. Check these the spruce is removed and the solvent is evaporated in vacuum. After purification via chromatography on a column (solvent: complex ethyl ester of acetic acid) gain of 7.4 g (83% of theory) of 2-amino-4-(fluoro-1-methyl-ethyl)-6-[3-(3, 5dimethylphenyl)-1-cyclobutyl-1 propylamino]-1,3,5-triazine.

Example A4

2-Amino-6-methyl-4-[3-(3-were)-1-cyclobutyl-1 propylamino]-1,3,5-triazine (see table 4, example 4-29)

2.2 g (0.015 mol) of 2-amino-4-chloro-6-methyl-ethyl)-1,3,5-triazine and 4.1 g (0.03 mol) of calcium carbonate are placed in 50 ml of acetonitrile. To this solution are added dropwise 2.5 g (0.015 mol) of 3-(3-were)-1-cyclobutyl-1-Propylamine dissolved in 20 ml of acetonitrile. Then the solution is boiled for 3 hours on the phlegm. Then the solid components were removed and the filtrate is passed through a centrifuge. The residue is purified via chromatography on a column (solvent: complex ethyl ester of acetic acid). Obtain 4.3 g (92% of theory) of 2-amino-6-methyl-4-[3-(3-were)-1-cyclobutyl-1 propylamino]-1,3,5-triazine.

Example A5

2-Amino-4-(1-fluoro-1-methyl-ethyl)-6-[4-(3, 5dimethylphenyl)-1-cyclopropyl-1 butylamino]-1,3,5-triazine (see table 22, the example 22-28)

To 8,4 g (0,025 mol) of 4-(3, 5dimethylphenyl)-1-cyclopropyl-1-(1-biguanidine)-butane-hydrochloride in 50 ml of methanol and 7 g of crushed molecular sieves 3 Angstrom add a solution of methanol obtained from 1.2 g (0.05 mol) of sodium and 100 ml of methanol. To the mixture are added dropwise to 5.4 g (0.045 mol) complex marked the CSOs ether 1-fluoro-1-methyl-propionic acid, and then stirred for 2 hours at a temperature of 25°and for 4 hours at a temperature of 65°C. the Reaction mixture is filtered, the filtrate concentrated and the residue is absorbed in a complex acetic ether. The mixture is then washed with water and dried using sodium sulfate. The desiccant is removed and the solvent is evaporated in vacuum. After purification via chromatography on a column (solvent: complex ethyl ester of acetic acid) to obtain 7.7 g (83% of theory) of 2-amino-4-(1-fluoro-1-methyl-ethyl)-6-[4-(3, 5dimethylphenyl)-1-cyclopropyl-1 butylamino]-1,3,5-triazine.

Compounds described in the following tables 1-44 receive according to or analogously to the above examples A1-A5 or other total of the above methods.

The abbreviations given in the tables represent:

Me=methyl

Et=ethyl

WG=cut

i-Pr=isopropyl

c-Pr=cyclopropyl

c-Bu=cyclobutyl

t-Bu=tertiary butyl

C-hexyl=cyclohexyl

A1=(CH2)1=-CH2-

A2=(CH2)2=-CH2CH2-

A3=(CH2)3=-CH2CH2CH2-

A4=(CH2)4=-CH2CH2CH2CH2-

AC=the PINES3=acetyl

Oh==oxiranyl

Ph=phenyl

(X)n=“-” corresponds to n=0

Table 1-41 comment General formula (I)

Table 1
No.R1-A2-R2And1(X)nPhysical data
1-1CH2-i-PrCH2-c-PrAl-oil
1-2CFMe2CH2-c-PrAl-oil
1-3i-PrCH2-c-PrAl-oil
1-4i-PrCH2-c-BuAl- 
1-5CFMe2CH2-c-BuAl- 
1-6MeCH2-c-BuAl- 
17 CFMe2CH2-c-BuAl3-IU 
1-8CFMe2CH2CH2from WGAl  
1-9i-PrCH2CH2from WGAl  
1-10CFMe2CH2CH2with VIAl  
1-11i-PrCH2CH2with VIAl  
Table 2
No.R1-A2-R2A1(X)nPhysical data
2-1c-Pr2,2-Cl2-c-PrA23-C1, 5-F 
2-2CFMe22,2-Cl2-c-PrA23-Me 
2-3l22,2-Cl2-c-PrA23-Me 
2-4CFMe22,2-Cl2-c-PrA23-Cl 
2-5i-Pr2,2-Cl2-c-PrA23-Cl 
2-6CFMe22,2-Cl2-c-PrA23-F 
2-7CHF22,2-Cl2-c-PrA23-F 
2-8CFMe22,2-Cl2-c-PrA23-OMe 
2-9l2 2,2-Cl2-c-PrA23-OMe 
2-10CFMe22,2-Cl2-c-PrCH2CHMe- 
2-11l22,2-Cl2-c-PrCH2CHMe- 

Table 3
No.R1-A2-R2A1(X)nPhysical data
3-1CFMe22-OMe-c-PrA2- 
3-2CFMe22-OEt-c-PrA2- 
3-3CF32,2-(OMe)2-c-PrA2- 
3-4CH2F2,2-(Et) 2-c-PrA2- 
Table 4
No.R1-A2-R2A1(X)nPhysical data
4-1i-Prc-BuA2-oil
4-2CFMe2c-BuA2-oil
4-3Mec-BuA2-oil
4-4Etc-BuA2- 
4-5Prc-BuA2- 
4-6Buc-BuA2- 
4-7 Phc-BuA2- 
4-8CH2-C6H5c-BuA2- 
4-9c-Prc-BuA2- 
4-10i-Prc-BuA23-Cloil
4-11CFMe2c-BuA23-Cloil
4-12CF3c-BuA23-Cl 
4-13CF3c-BuA2- 
4-14i-Prc-BuA23-Meoil
4-15 CFMe2c-BuA23-Meoil
4-16CF3c-BuA23-Me 
4-17CCl3c-BuA23-Me 
4-18Mec-BuA22-Me 



4-19
Etc-BuA22-Me 
4-20CH2-i-Prc-BuA22-Me 
4-21With6H5c-BuA22,4-Cl2 
4-22CH2-Phc-BuA24-NO2 
4-23i-RGc-BuA23-OMeoil
4-24F2c-Bu A23-OMeoil
4-25CFMe2c-BuA22-Meoil
4-26i-Prc-BuA22-Meoil
4-27i-Prc-BuA23-Foil
4-28CFMe2c-BuA23-Foil
4-29Mec-BuA23-Meoil

Table 5
No.R1-A2-R2A1(X)nPhysical data
5-1CFMe22,2,3,3-F4-c-BuA2- 
5-2CHFMe2,2,3,3-F4-c-BuA2- 
5-3CF(CF3)22,2,3,3-F4-c-BuA2- 
5-4l22,2,3,3-F4-c-BuA2- 
5-5i-Pr2,2,3,3-F4-c-BuA2- 
Table 6
No.R1-A2-R2A1(X)nPhysical data
6-1CFMe23-OH-c-BuA2- 
6-2i-Pr3-OH-c-BuA2- 
6-3CFMe23-OH-c-BuA23-Me 
6-4CF33-OH-c-BuA23-Me 
6-5Et3-OH-c-BuA23,5-Me2 

6-6Et3-OH-c-BuA2 3,5-Me2 
6-7CFMe23-Ac-c-BuA2- 
6-8CFMe23-och3-C6H4with VIA2- 
6-9Me3,3-F2-c-BuA2- 
6-10Pr3,3-F2-c-BuA2- 
6-11CFMe23,3-F2-c-BuA2- 
6-12Et3,3-F2-c-BuA2- 
6-13CF33,3-F2-c-BuA2 - 
6-14CH2F3-Me-c-BuA2- 
6-15CF33-Me-c-BuA2- 
Table 7
No.R1-A2-R2A1(X)nPhysical data
7-1CFMe2A2-
7-2i-PrA2-
7-3CF3A2-
7-4 CH2FA2-
7-5CclMe2A2-
Table 8
No.R1-A2-R2And1(X)nPhysical data
8-1i-Prwith pencilA2-oil
8-2CFMe2with pencilA2-oil

Table 9
No.R1-A2-R2A1(X)nPhysical data
9-1CH2-i-Prc-PrA2 -oil
9-2Etc-PrA2-oil
9-3Mec-PrA2-oil
9-4CMe2CsNc-PrA2-oil
9-5CFMe2c-PrA23-Foil
9-6CFMe2c-PrA23-CF3oil
9-7i-Prc-PrA23-Cloil
9-8CFMe2c-PrA23-Cloil
9-9i-Prc-PrA2-oil
9-10CFMe2c-PrA2-oil
9-11i-Prc-PrA23-CF3oil
9-12i-Prc-PrA23-Meoil
9-13i-Prc-PrA2 3-OMeoil
9-14CFMe2c-PrA23-OMeoil
9-15CH2-i-Prc-PrA23-Meoil
9-16CFMe2c-PrA23-Meoil
9-17CFMe2c-PrA23,5-Me2oil
9-18i-Prc-PrA23,5-Me2oil
9-19With6H5c-PrA2-oil
9-20CFMe2c-Pr-CH2-CO--oil
9-21i-Prc-Pr-CH2-CO--oil
9-22CF(CF3)2c-Pr-CH2-CO--oil

Table 10
No.R1-And2-R2And1(X)n Physical data
10-1CFMe22,2-Me2from WGA2-oil
10-2i-Pr2,2-Me2from WGA2- 
10-3CFMe22,2-Me2from WGA23-CL 
10-4(F)(OMe)-CF32,2-Me2from WGA23-CL 
10-5CH32,2-Me2from WGA22,3-Cl2 
10-6CFMe22,2-Me2from WGA2the 3.5-F2 
10-7CFMe22,2-Me2from WGA23-F 
10-8i-Pr2,2-Me2from WGA23-F 
10-9CFMe22,2-Me2from WGA23-OMe 
10-10CF32,2-Me2from WGA23-OMe 
10-11CFMe22,2-Me2from WGA23-IU 
10-12CH2CHF22,2-Me2from WGA23-IU 
10-13CFMe22,2-Me2from WG- 
10-14CF32,2-Me2from WG- 
10-15CHF22,2-Me2from WGCH2-Snme-- 
10-16CclMe22,2-Me2from WGCH2-CHMe-- 

A2
Table 11
No.R1-A2-R2A1(X)nPhysical data
11-1CFMe22,2-F2-c-PrA2- 
11-2 CH32,2-F2-c-PrA2- 
11-3CFMe22,2-F2-c-PrA23-Cl 
11-4i-Pr2,2-F2-c-PrA23-Cl 
11-5CFMe22,2-F2-c-PrA23-F 
11-6CF(CF3)22,2-F2-c-PrA23-F 
11-7CFMe22,2-F2-c-PrA23-OMe 
11-8CH2-i-Pr2,2-F2-c-PrA23-OMe 
11-9CFMe22,2-F2-c-PrA23-CF3 
11-10 CFMe22,2-F2-c-PrA23-CCL3 
11-11CFMe22,2-F2-c-Pr-CH2CHOH-- 
11-12C(OMe)Me22,2-F2-c-Pr-CH2CHOH-- 
11-13CClMe22,2-F2-c-Pr-CH2CHOAc-- 
11-14Me2,2-F2-c-Pr-CH2CHOAc-- 
Table 12
No.R1-A2-R2And1(X)nPhysical data
12-1CFMe22,2-Br2-c-PrA2- 
12-2CF2CHF22,2-Br2-c-Pr- 

Table 13
No.R1-A2-R2And1(X)nPhysical data
13-1MeC-hexylA2- 
13-2CH2FC-hexylA2- 
13-3CF3C-hexylA23-OH 
13-4CCl3C-hexylA23-OEt 
13-5CHFMeC-hexylA23-OPh 
13-6c-PrC-hexylA2- 
13-7CH2-C6H5C-hexylA2- 
Table 14
No. R1-A2-R2A1(X)nPhysical data
14-1MeOxA2- 
14-2EtOxA2- 
14-3PrOxA2- 
14-4i-PrOxA2- 
14-5CFMe2OxA2- 
14-6CF3OxA23-Cl 
14-7CFMe2OxA23-Cl 
14-8i-PrOxA23-Cl 
14-9CFMe2OxA23-OMe 
14-10i-PrOxA23-OMe 
14-11CFMe2OxA23-F 
14-12i-PrOxA23-F 

Table 15
No.R1-A2-R2A1(X)nPhysical data
15-1CFMe1-Me-OxA2- 
15-2i-RG1-Me-OxA2- 
15-3Me1-Me-OxA2- 
15-4c-Pr1-Me-OxA2- 
15-5Ox1-Me-OxA22-NO2 
Table 16
No.R1-A2-R2A1(X)nPhysical data
16-1n-Pr1,2-Me2-OhA23-OH 
16-23,5-CL2-C6H31,2-Me2-OhA24-HE 
16-3c-Pr2-Me-OhA25-OEt 
16-4CH2-4-C1-C6H42-Me-OhA25-SMe 
Table 17
No.R1-A2-R2A1(X)nPhysical data
17-1CFMe2A2- 
17-2CF2CHF2A2- 
17-3CH2PhA2- 

Table 18
No.R1-A2-R2And1(X)nPhysical data
18-1CFMe23-furyl A2-oil
18-2i-Pr3-furylA2-oil
18-3CFMe2With6H5A2-oil
18-4i-PrWith6H5A2-oil

Table 19
No.R1-A2-R2And1(X)nPhysical data
19-1A22-HE 
19-2CH2-c-PrA2- 
19-3A2- 
19-4(N)(SN3)-C2H5A2- 
19-5 CFMe2A2-oil
19-6i-PrA2-oil

Table 20
No.R1-A2-R2A1(X)nPhysical data
20-1CFMe2A2-oil
20-2i-PrA2-oil
Table 21
No.R1-A2-R2And1(X)nPhysical data
21-1MeA2- 
21-2CF3A2- 
21-3CHFMe - 
21-4CFMe2A2- 
21-5Cl2A2- 
21-6CFMe2A2- 
21-7CF2Cl3A2- 

Table 22
No.R1-A2-R2A1(X)nPhysical data
22-1CHClMec-PrA3- 
22-2CHClMec-PrA3- 
22-3CHFMec-PrA3-oil
22-4CF2CF3c-PrA3- 
22-5CF2 CHF2c-PrA33-NO2 
22-6CF3c-PrA32,4-Cl2oil
22-7CCl3c-PrA3- 
22-8Mec-PrA3-oil
22-9Etc-PrA3-oil
22-10Prc-PrA3- 
22-11i-Prc-PrA3-oil
22-12CFMe2c-PrA3-oil
22-13With6H5c-PrA3- 
22-14CFMe2c-PrA32-Cl 
22-15i-Prc-PrA32-Cl 
22-16CFMe2c-PrA32,4-Cl2 
22-17i-Prc-PrA32,4-Cl2 
22-18CFMe2c-PrA33-Cloil
22-19i-Prc-PrA33-Cl 
22-20i-Prc-PrA33,5-Cl2 
22-21CFMe2c-PrA33,5-Cl2 
22-23CFMe2c-PrA32-F 
22-24CFMe2c-PrA33-Foil
22-25i-Prc-PrA33-Foil
22-26i-Prc-PrA33-Meoil
22-27CFMe2c-PrA33-Meoil
22-28CFMe2c-PrA33,5-Me2oil

A3
2-29 i-Prc-PrA33-OMeoil
22-30CFMe2c-PrA33-OMeoil
22-31CF3c-PrA3-oil
Table 23
No.R1-A2-R2And1(X)nPhysical data
23-1CFMe2A3- 
23-2l2A3- 
23-3CHFMe- 
Table 24
No.R1-A2-R2A1(X)nPhysical data
24-1CFMe22,2-F2-c-PrA3- 
24-2i-Pr2,2-F2-c-PrA3- 
24-3CFMe22,2-F2-c-PrA33-Cl 
24-4CFMe22,2-F2-c-PrA33,5-Cl2 
24-5CFMe22,2-F2-c-PrA33-Me 
2-6 CFMe22,2-F2-c-PrA33-Br 
24-7CFMe22,2-F2-c-PrA33-F 
24-8CFMe22,2-F2-c-PrA3the 3.5-F2 
24-9CFMe22,2-F2-c-PrA33-OMe 
24-10CFMe22,2-F2-c-PrA33-OH 

Table 25
No.R1-A2-R2And1(X)nPhysical data
25-1CFMe22,2-Cl2-c-PrA3-  
25-2CFMe22,2-Cl2-c-PrA33-Cl 
Table 26
No.R1-A2-R2A1(X)nPhysical data
26-1CFMe22,2-Me2-c-PrA3- 
26-2CFMe22,2-Me2-c-PrA3- 
26-3CFMe22,2-Me2-c-PrA33-F 
26-4CFMe22,2-Me2-c-PrA33-Me 
26-5CFMe22,2-Me2-c-PrA33-OMe 
26-6CFMe22,2-Me2-c-PrA33-Cl 
Table 27
No.R1-A2-R2 A1(X)nPhysical data
27-1Me2,2,3,3-F4-c-BuA3- 
27-2(CH2)4-CH32,2,3,3-F4-c-BuA3- 
27-3CFMe22,2,3,3-F4-c-BuA3- 

td align="center"> CFMe2
Table 28
No.R1-A2-R2A1(X)nPhysical data
28-1Mec-BuA3- 
28-2Etc-BuA3- 
28-3Prc-BuA3- 
28-4i-Prc-BuA3-oil
28-5i-Buc-BuA3-oil
28-6CH2-i-Ptc-Bu A3- 
28-7CF3c-BuA3- 
28-8CH2Fc-BuA3- 
28-9CF2CHF2c-BuA3- 
28-10CFMe2c-BuA3-oil
28-11i-Prc-BuA34-NO2 
28-12CFMe2c-BuA32-CF3 
28-13i-Prc-BuA33-Cloil
28-14CFMe2c-BuA33-Cloil
28-15i-Prc-BuA33-CF3 
28-16CFMe2c-BuA3C-CF3 
28-17i-Prc-BuA33-Meoil
28-18c-BuA33-Meoil
28-18i-Prc-BuA33-F 
28-19CFMe2c-BuA33-F 
28-20i-Prc-BuA33-OMeoil
28-21CFMe2c-BuA33-OMeoil
28-22CFMe2c-Bu-CH2CHNMe2-- 
28-23CFMe2c-Bu-CH2CHNMe2-- 

CFMe2
Table 29
No.R1-A2-R2A(X)nPhysical data
29-1CFMe2OxA3- 
29-2i-PrOxA3- 
29-3CFMe2 OxA33-Cl 
29-4c-PrOxA33-Cl 
29-5CFMe2OxA33,5-Cl2 
29-6CFMe2OxA33-F 
29-7CFMe2OxA33-Me 
29-8CFMe-OxA33-OMe 
29-9CFMe2OxA33-F 
29-10CFMe2OxA3the 3.5-F2 
Table 30
No.R1-A2-R2And1(X)nPhysical data
30-1i-Prc-PrA4-oil
30-2c-PrA4-oil
30-3CFMe22,2-Cl2-c-PrA4- 
30-4CF32,2-F2-c-PrA4- 
Table 31
No.R1-A2-R2A1(X)nPhysical data
31-1CFMe2c-BuA4-oil
31-2CF3c-BuA4- 
31-3i-Prc-BuA4-oil

Table 32
No.R1-A2-R2A1(X)nPhysical data
32-1i-PrCH2From WGA -oil
32-2CFMe2CH2From WGA2-oil
32-3i-PrCH2From WGA23-Br 
32-4CFMe2CH2From WGA23-Br 
32-5i-PrCH2From WGA23-Cloil
32-6CFMe2CH2From WGA23-Cloil
32-7i-PrCH2From WGA23-F 
32-8CFMe2CH2From WGA23-F 
32-9i-PrCH2From WGA23-Meoil
32-10CFMe2CH2From WG A23-Meoil
32-11i-PrCH2From WGA23-OMeoil
32-12CFMe2CH2From WGA23-OMeoil
32-13CFMe2CH2From WG-CH2-CHOMe-- 
32-14CF3CH2From WG-CH2-CHOEt-- 
32-15CH2FCH2From WG-CH2-CHOAc-- 
32-16CHF2CH2From WG-CH2-CHOMe-- 
32-17CHF2CH2From WG-CH2-CH(OCOEt)-- 
32-18CFMe2CH2From WG-CH2-CHSMe-2-Cl
32-19CClMe2CH2From WG-CH2-CHSEt-2,5-Cl2 
Table 33
No.R1-A2-R2A1(X)nPhysical data
33-13,5-CL2-C6H3CH2-2,2-F2-c-PrA2- 
33-2CFMe2CH2-2,2-F2-c-PrA2-oil
33-3i-PrCH2-2,2-F2-c-PrA2-oil

 
33-4EtCH2-2,2-F2-c-PrA2- 
33-5CFMe2CH2-2,2-F2-c-PrA23-Cl
33-6i-PrCH2-2,2-F2-c-PrA23-Cl 
33-7CFMe2CH2-2,2-F2-c-PrA23-OMe 
33-8CFMe2CH2-2,2-F2-c-PrA23-Me 
33-9CFMe2CH2-2,2-F2-c-PrA23-F 
33-10CFMe2CH2-2,2-F2-c-PrA23-I 
33-12CFMe2CH2-2,2-F2-c-PrA23-Br 
33-13CFMe2CH2-2,2-F2-c-PrA23-Cl,3-F 
Table 34
No. R1-And2-R2A1(X)nPhysical data
34-1CFMe2CH2-(2,2-Cl2-c-Pr)A2- 
34-2i-PrCH2-(2,2-Cl2-c-Pr)A2- 
34-3CFMe2CH2-(2,2-Cl2-c-Pr)A23-F 
34-4CF(CF3)2CH2-(2,2-Cl2-c-Pr)A23-F 
34-5CFMe2CH2-(2,2-Cl2-c-Pr)A23-Cl 
34-6Cl2CH2-(2,2-Cl2-c-Pr)A23-Cl 
34-7CFMe2CH2-(2,2-Cl2-c-Pr)A23-Me 
34-8MeCH2-(2,2-Cl2-c-Pr)A23-Me 
Table 35
No.R1-A2-R2A1(X)nPhysical data
35-1CFMe2CH2-c-BuA2- 
35-2i-PrCH2-c-BuA2- 
35-3CH3CH2-c-BuA2- 
35-4CF3CH2-c-BuA2 - 

td align="center"> 36-7
35-5Cl2CH2-c-BuA2- 
35-6CHFMeCH2-c-BuA2- 
Table 36
No.R1-AWA1(X)nPhysical data
36-1CF2CF3-CHOH-c-PrA2- 
36-2CF2CHF2-CHOH-c-PrA2- 
36-3CFCl2-CHOH-c-PrA2- 
36-4CFMe2-CHOH-c-PrA2- 
36-5CFMe2-CHOH-c-PrA23-Cl 
i-Pr-CHOH-c-BuA2- 
36-8CFMe2-CHOH-c-BuA2- 
36-9Me-CHOMe-c-PrA2- 
36-10CF3-CHOMe-c-BuA2- 
Table 37
No.R1-A2-R2A1(X)nPhysical data
37-1CF3CH2-OhA2- 
37-2CFMe2CH2-OxA2- 
37-3i-PrCH2-OhA2- 

Table 38
the R1-A2-R2And’(X)nPhysical data
38-1CH2FA2- 
38-2CHF2A2- 
38-3CClF2A2- 
38-4CFMe2A2- 
38-5i-PrA2- 
38-6CFMe2A2- 
38-7CFMe2A2- 
38-8i-PrA2- 
Table 39
No.R1-A2-R2A1(X)nPhysical data
39-1(D)(OMe)-CF3A24-CN 
39-2CF(OEt)CF3A23-och3 
39-3CFMe2A23-Cl 

39-4 CFMe2A2- 
39-5EtA2- 
Table 40
No.R1-A2-R2And1(X)nPhysical data
40-1CFMe2CH2-OhA33-CL 
40-2CFMe2CH2-OhA33-IU 
40-3CFMe2CH2-OhA33-CFC 
40-4CFMe2CH2-OhA3 3-F 
Table 41
No.R1-A2-R2And1(X)nPhysical data
41-1CHMeEtCH2-CH2-OHA23,5-F2 
41-2CFMe2CH2-CH2-OHA2- 
41-3CFMe2(CH2)2from WGA2- 
41-4c-Pr(CH2)2from WGA22,4-Br2 
41-5CH3CH2CHOH-c-BuA2- 
1-6 CH2CLCH2SNON-with-VIA2- 
41-7CH2FA2- 
41-8CFMe2CH2CH2-c-BuA2- 
41-9CFMe2A2- 

41-10CFMe2A2- 
41-11CFMe2A2- 
41-12CFMe2A2- 
41-13CFMe2 A2- 
41-14CFMe2A2- 
41-15CFMe2A2- 
41-16CFMe2A2- 
41-17CFMe2A2- 
41-18CFMe2A2- 

Table 42: compounds of the formula (II)
No.R1-A2-R2R3A1(X)nPhysical data
42-1MeOxMeA2- 
42-2CFMe2c-PrEt A22.4-Cl2 
42-3CFMe2c-Pri-PrA2- 
42-4i-Prc-BuNH-MeA2- 
42-5i-Prc-BuNH-EtA2- 
42-6MeCH2-c-BuNme2A34-Cn 
42-7EtCH2-c-BuNEt2A34-Et 
42-8Mec-BuHA34-i-Pr 
42-9Etc-BuHA34-c-Pr 
42-10CFMe2CH2-c-PrNHAcA2- 
42-11CClMe2CH2from WGNHCOEtA2- 
42-12CH2-c-PrCH2-c-BuNHCOPhA2 - 

Table 43: the compounds of formula (III)
No.R1-A2-R2R3R4A1(X)nPhysical data
43-1CH(OMe)Mewith pencilNH2NHAcA2- 
43-2CH(OEt)Mewith pencilNH2NHCHOA2- 
43-3CMe2CNc-BuNH2NHCOEtA2- 
43-4CMe2-SMec-BuNH2EtA2- 
43-5CFMe2c-BuNH2MeA2- 
43-6CHFMec-PrNH2n-PrA3- 
43-7CHClMec-PrNH2n-BuA3- 
Table 44: the compounds of formula (IV)



No.
R1-A2-R2(X)nZPhysical data
44-1CFMe2c-Pr-Hoil
44-2i-Prc-Pr-Hoil
44-3Mec-Pr-H 
44-4CFMe2c-Pr3-ClH 
44-5i-Prc-Pr3-ClH 
44-6CFMe2c-Pr3-CH3H 
44-7CFMe2c-Pr3-CH3H 
44-8CFMe2c-Pr -Br 
44-9CFMe2c-Pr-Br 
44-10i-Prc-Pr-Br 
44-11CFMe2c-Pr-Cl 
44-12i-Prc-Pr-Cl 
44-13F3c-Pr-Cl 
44-14CFMe2c-Bu-H 
44-15i-Prc-Bu-H 
44-16CFMe2i-Bu-Cl 
44-17CFMe2c-Bu-Br 
44-18F3t-Bu-Cl 
44-19Ft-Bu-Br 
44-20CFMe2c-Pr -Me 
44-21CH3c-Pr-Me 
44-22CFMe2c-Bu-Me 

The data of nuclear magnetic resonance for the individual examples:

for example 4-2:

1H-NMR (DMSO-d6):δ=1.5 (singlet, 3H), 1,6 (singlet, 3H), 1.5 to 2.0 (multiplet), 2,4-2,6 (multiplet), 4,0 (multiplet, 1H), 7,2 (multiplet, 5H)

Example 4-28:

1H-NMR (CDCl3): δ=1,6 (s, 3H), 1,7 (s, 3H), of 1.5-1.9 (m)to 2.4 (m, 2H), 2,6-2,7 (m, 2H), 4,1 (m, 1H), 4,1 (m, 1H), 6,8-7,0 (m, 3H), 7,2 (m, 1H)

Example 4-27:

1H-NMR (CDCl3): δ=1,6 (s, 3H), 1,7 (s, 3H), 1.7 to 1.9 (m, 6H), and 2.6 (m, 2H), 4,0 (m, 1H), 6,9 (m, 3H), 7,2 (m, 1H)

Example 8-2:

1H-NMR (CDCl3): δ=1,6 (s, 3H), 1,7 (s, 3H), 1.5 and 1.8 (m, 10H), and 2.6 (m, 2H), 4,0 (m, 1H), 7,2 (m, 5H)

Example 9-1:

1H-NMR (CDCl3): δ=0,2-0,6 (m, 4H), and 0.9 (m, 1H), 1,2 (m, 3H), and 2.7 (m, 1H), 3,5 (m, 1H), 7,2 (m, 5H)

Example 9-8:

1H-NMR (CDCl3): δ=0,2-0,6 (m, 4H), and 0.9 (m, 1H), and 1.6 (s, 3H), 1,7 (s, 3H), 2,0 (m, 2H), and 2.7 (m, 2H), 3,5 (m, 1H), 7,2 (m, 4H)

Example 9-14:

1H-NMR (CDCl3): δ=0,2-0,6 (m, 4H), and 0.9 (m, 1H), 1,6 (m, 1H), and 1.6 (s, 3H), 1,7 (s, 3H), and 2.7 (m, 2H), 3,5 (m, 1H), 3,9 (s, 3H), 6,8 (s, 4H)

Example 9-18:

1H-NMR (CDCl3): δ=1,2 (m, 6H), 2,3 (s, 6H), to 2.7 (m, 2H), 3,5 (m, 1 H), 6,8 (m, 3H)

Example 20-1:

1H-NMR (CDCl3): δ=1,6 (s, 3H), 1,7 (s, 3H) 1,7-2,0 (m, 4H), and 2.7 (m, 2H), 3,6-3,9 (m, 4H), 4,1 (m, 1H), 7,2 (m, 5H)

Example 18-1:

1H-NMR (DMSO-d6): δor=1.5 (s, 3H), and 1.6 (s, 3H), 1,7-2,1 (m, 2H), 2,5-2,6 (m, 2H), 5,0 (m, 1H), of 7.2 to 7.7 (m, 8H)

Example 22-3:

1H-NMR (DMSO-d6): δ=0,1 (m, 1H), 0,3 (m, 2H), 0,4 (m, 1H), and 0.9 (m, 1H), 1.5 a (s, 3H), and 1.6 (s, 3H), 3.5 m (1H), a 7.1 to 7.3 (m, 5H)

Example 22-8:

1H-NMR (DMSO-d6): δ=0,1-0,5 (m, 4H), and 0.9 (m, 1H), 2,0 (s, 3H), 3,5 (m, 1H), 7,2 (m, 5H)

Example 22-18:

1H-NMR (CDCl3): δ=0,2-0,6 (m, 4H), and 0.9 (m, 1H), and 1.6 (s, 3H), 1,7 (s, 3H), 2,8 (m, 2H), 3,5 (m, 1H), 7,2 (m, 4H)

Example 22-25:

1H-NMR (CDCl3): δ=0,2-0,6 (m, 4H), 0.8 a (m, 1H), 1,2 (d, 6H), of 1.6-1.8 (m, 4H), to 2.5-2.7 (m, 2H), 3,5 (m, 1H), 6,9 (m, 3H), 7,2 (m, 1H)

Example 22-27:

1H-NMR (CDCl3): δ=0.2 to 0.5 (m, 4H), and 0.9 (m, 1H), 1.5 a (s, 3H), and 1.6 (s, 3H), 2,3 (s, 3H), 2,5 (m, 2H), 3,5 (m, 1H), 7,0 (m, 3H), and 7.1 (m, 1H)

Example 28-10:

1H-NMR (DMSO-d6): δor=1.5 (s, 3H), and 1.6 (s, 3H), of 1.5-1.9 (m), and 2.6 (m)4,0 (m, 1H), 7,1-7,3 (m, 5H)

Example 30-2:

1H-NMR (CDCl3): δ=0,2-0,6 m (4H), of 0.8-1.0 (m, 3H), 1,4 (m, 2H), 1.5 a (s, 3H), 1,7 (s, 3H), and 2.6 (t, 2H), 3,5 (m, 1H), 7,1-7,3 (m, 5H)

Example 31-1:

1H-NMR (CDCl3): δ=1,6 (s, 3H), 1,7 (s, 3H), 1,7-2,0 (m, 6H), and 2.6 (m, 2H), 4,0 (m, 1H), 7,2 (m, 5H)

Example 32-2:

1H-NMR (DMSO-d6): δ=0,1 (m, 2H), and 0.4 (m, 2H), 0,7 (m, 1H), 1.5 a (s, 3H), and 1.6 (s, 3H), 1.8 m (m, 2H), and 2.6 (m, 2H), 4,0 (m, 1H), 7,2 (m, 5H)

Example 32-9:

1H-NMR (DMSO-d6): δ=0,1 (m, 2H), and 0.4 (m, 2H), 0,7 (m, 1H), 1,1 (d, 6H), 1,6 (m, 2H), 1.8 m (m, 2H), 2,3 (s, 3H), 4,0 (m, 1H), 7,0 (m, 3H), 7,2 (m, 1H)

Example 32-10:

1H-NMR (VHI is-d 6): δ=0,1 (m, 2H), and 0.4 (m, 2H), 0,7 (m, 1H), 1.5 a (s, 3H), and 1.6 (s, 3H), 1.8 m (m, 2H), 2,3 (s, 3H), 4,0 (m, 1H), 7,0 (m, 3H), 7,2 (m, 1H)

Example 32-12:

1H-NMR (DMSO-d6): δ=0,1 (m, 2H), and 0.4 (m, 2H), 0,7 (m, 1H), 1,2 (d, 6H), 1,4 (m, 3H), 1.8 m (m, 2H), 2.5 and 2.7 (m, 2H), and 3.7 (m, 3H), 4,0 (m, 1H), 6,7 (m,3H), 7,2 (m, 1H)

Example 33-3:

1H-NMR (DMSO-d6): δ=1,1 (d, 6H), of 1.5-1.9 (m), to 2.5-2.7 (m)4,1 (m, 1H), 7,1-7,3 (m, 5H)

Example 44-1

1H-NMR (DMSO-d6): δ=0.2 to 0.5 (m, 4H), 1.5 a (s, 3H), and 1.6 (s, 3H), 4,2 (m, 2H), and 6.3 (dd, 1H), 6,5 (d, 1H), 7,2 (m, 5H)

Example 4-1:

1H-NMR (DMSO-d6): δ=1,2 (s, 6H), 1.5 to 2.0 (m, 6N), 2,4-2,7 (m, 2H), 4,0 (m, 1H), 7,2 (m, 5H)

Example 4-10:

1H-NMR (DMSO-d6): δ=1,2 (s, 6H), of 1.5-1.9 (m, 6H), 2,4-2,6 (m, 2H), 4,0 (m, 1H), 7,2 (m, 4H)

Example 4-11:

1H-NMR (CDCl3): δor=1.5 (s, 3H), and 1.6 (s, 3H), 1,7-2,0 (m, 6H), and 2.6 (m, 2H), 4,0 (m, 1H), 7,2 (m, 4H)

B. Examples of reporting forms

a) Mix 10% of the mass. the compounds of formula (I) and 90% of the mass. talc as inert substance), the mixture is ground in a hammer mill and get a pollinating agent.

b) Mix 25% of the mass. the compounds of formula (I), 64% of the mass. quartz containing kaolin (an inert substance), 10% of the mass. potassium ligninsulfonate acid and 1% of the mass. sodium railneteurope acid (as a wetting and dispersing agent), process in a rod mill and get a wettable powder which is easily dispersible in water.

C) Mix 20% of the mass. the compounds of formula (I) is 6% of the mass. simple al-celenapravlennogo ether (EO) and 71% of the mass. paraffinic mineral oil (boiling range, for example, about 255-277° (C)are processed in friction ball mill with grinding less than 5 microns and obtained dispersion concentrate which is easily dispersible in water.

g) Mixed 15% of the mass. the compounds of formula (I), 75% of the mass. cyclohexanone as solvent and 10% of the mass. atsetilirovanie of Nonylphenol as emulsifier) and get emulsifying concentrate.

d) Mixed

75% of the mass. the compounds of formula (I),

10% of the mass. calcium ligninsulfonate acid,

5% of the mass. laurylsulphate sodium

3% of the mass. polyvinyl alcohol and

7% of the mass. kaolin,

process in a rod mill, powder granularit in the vortex layer by spraying water as a granulating solution) and get a granulated product dispersible in water.

e) 25% of the mass. the compounds of formula (I),

5% of the mass. sodium 2,2’-dentalimplant-6,6’-disulfonic acid,

2% of the mass. sodium railneteurope acid,

1% of the mass. polyvinyl alcohol,

17% of the mass. calcium carbonate and

50% of the mass. water

homogenized and milled in a colloid mill, and then processed in a bead mill, thus obtained suspension pulverizer and dried in a scrubber using a one-component SOP is and get granular product, dispersible in water.

C. Biological examples

1. Management of weeds before you shoot

Seeds krestotsvetnyh and grass weeds are placed in plastic pots with Speakon and covered with earth. The proposed compound (prepared as wettable powders or emulsion concentrates) is injected in the form of aqueous suspensions or emulsions at different doses, flow rates of 600-800 l/ha on the surface of the earth. After treatment, the pots are placed in a greenhouse and regulate conditions favorable for weed growth.

3-4 weeks after germination of the experimental plants perform visual analysis of the damage to the plants or seedlings compared to untreated control samples. As the results show, the compounds demonstrate good herbicide activity at predsjedava method of processing a wide range of grasses and weeds. When you study the examples, for example, No. 4-1, 4-2, 4-3, 4-10, 4-11, 4-14, 4-15, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 8-1, 8-2, 9-1, 9-2, 9-3, 9-4, 9-5, 9-6, 9-7, 9-8, 9-9, 9-10, 9-11, 9-12, 9-13, 9-14, 9-15, 9-16, 9-17, 9-18, 9-19, 10-1, 18-1, 18-2, 18-3, 18-4, 19-5, 19-6, 20-1, 20-2, 22-3, 22-6, 22-8, 22-9, 22-11, 22-12, 22-18, 22-24, 22-25, 22-26, 22-27, 22-28, 22-29, 22-30, 22-31, 28-4, 28-5, 28-10, 28-13, 28-14, 28-17, 28-18, 28-20, 28-21, 30-1, 30-2, 31-1, 31-2, 31-3, 32-1, 32-2, 32-5, 32-6, 32-9, 32-10, 32-11, 32-12, 33-2, 33-4, 44-1 and 44-2 (see table 1-44) in predsjedava the processing method show excellent herbicide activity on the wearing of harmful plants, as, for example, starwort average, darnel ryegrass mnogotonny, amaranth thrown back, white mustard, oats and spickle green, at a flow rate of the active substance of 1 kg or less per hectare. (see Table B.1).

2. Management of weeds post-emergent.

Seeds of monocotyledonous and dicotyledonous weeds are placed in plastic pots with spescom, covered with earth and placed in a greenhouse where they regulate the conditions favorable for weed growth. Three weeks after sowing proposed connections process pilot plants that are in stage 3 sheets. The proposed connection is made in the form of a powder or emulsion concentrates, in different doses sprayed onto the green parts of plants when the water flow 600-800 l/ha 3-4 weeks experienced plants kept in the greenhouse under optimum conditions for growth, and then conduct a visual analysis of the action of the drug compared with untreated control samples. When the post-harvest processing method proposed agent also demonstrates good herbicide activity against a broad spectrum of grasses and weeds. When you study the examples, for example, No. 4-1,4-2, 4-3, 4-10,4-11, 4-14, 4-15, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 8-1, 8-2, 9-1, 9-2, 9-3, 9-4, 9-5, 9-6, 9-7, 9-8, 9-9, 9-10, 9-11, 9-12, 9-13, 9-14. 9-15, 9-17, 9-18, 9-19, 10-1, 18-1, 18-2, 18-3. 18-4, 19-6, 20-1, 20-2, 22-3, 22-6, 22-8, 22-9, 22-11, 22-12, 22-18, 22-24, 22-25, 22-26, 22-27, 22-28, 22-29, 22-30,22-31, 28-4, 28-5, 28-10, 28-13, 28-14, 28-17, 28-18, 28-20, 28-21, 30-1, 30-2, 31-1, 31-2, 31-3, 32-1, 32-2, 32-5, 32-6, 32-9, 32-10, 32-11, 32-12, 33-2, 33-4, 44-1 and 44-2 (see table 1-44) in the post-harvest processing method show excellent herbicide activity against harmful plants, such as mustard white, barnyard grass chicken millet, ryegrass ryegrass mnogotonny, starwort average, syt, amaranth thrown back, spickle green and oats at the rate of the active substance of 1 kg or less per hectare.

3. Processing shoots noxious plants.

Planted and blossomed shoots typical of grasses and weeds in closed plastic pots are placed in a greenhouse until reaching stage 3 sheets (barnyard grass chicken millet 1.5 sheet), provided that the height of water over the plants were 2-3 cm Then spend processing the proposed connections. This is composed of the active substance is suspended in water, dissolve or emuleret and in different doses, method of irrigation is injected into the water over the experimental plants. After this treatment pilot plants are placed in a greenhouse under conditions of optimal growth and maintain during the entire testing time.

About three weeks after treatment prodat optical analysis of plant damage compared to untreated control samples. The proposed compounds have excellent herbicide activity is ü against harmful plants. In the study, for example, the compounds of examples No. 4-1,4-2, 4-14, 4-15, 4-23, 4-24, 9-4, 9-5, 9-9, and 9-10 9-7 (see table 1-44) demonstrate excellent herbicide activity against harmful plants, which are typical for crops such as, for example, syt, barnyard grass chicken millet and arrowheads.

4. The compatibility of the proposed connections with cultivated plants.

In the following experiments in the greenhouse, seeds of cultivated plants (in larger quantities) and weeds lay in speak and covered with earth. Part of the pots treated immediately as described in section 1, the other placed in a greenhouse until the plants reached the stage of 2-3 leaves, and then, as describe in section 2, spray the proposed substance of the formula (I) in various doses. After 4-5 weeks after treatment and maturing in the greenhouse are conducting optical analysis, which shows that the proposed connection at predsjedava or post-harvest processing and high doses of the active substances are harmless to dudleston crops such as soybean, cotton, canola, sugar beet and potatoes. Moreover, some substances contribute to the preservation of such cereals, such as barley, wheat, rye, sorghum, corn and rice. Some of the compounds of formula (I) exhibit high selectivity and are therefore suitable for combat ROSTO is undesirable plants in crops.

Biological data

Are shown in the following table. B.1 receive the data specified in the example

B.1 (see pages 100-101).

Table B.1: control weeds before shoot
Example. No.the consumption rate in g/hathe degree of destruction in %
  STEMELOLMUSETVIAMAREECHCG
4-1320100100100100100
4-2320100100100100100
4-10320100100100100100
4-11320100100100100100
4-17320100100100100100
4-28320100100100100100
8-2320100100100100100
9-2320100100100100100
9-8320100100100100100
9-14320100100100100100
9-18320100100100100100
18-1320100100100100100
20-1320100100100100100
22-3320100100100100100
22-8320100100100100100
22-18320100100100100100
22-25320100100100100100
22-27320100100100100100
28-10 320100100100100100
30-2320100100100100100
31-1320100100100100100
32-2320100100100100100
32-9320100100100100100
32-10320100100100100100
32-12320100100100100100
33-3320100100100100100
44-1320100100100100100
abbreviations:

STEME = Stellaria media, LOLMU = Lolium Polygonum, SETVI = Setaria viridis, AMARE = Amaranthus retroflexus, ECHCG = Echinochloa crus-galli.

1. Derivatives of 2-amino-1,3,5-triazine of the formula (I)

in which R1means phenyl isoalkyl with 1 to 6 carbon atoms, which may be substituted by one or more radicals from the group halogen and cyano;

R2means cyclopropyl, cyclobutyl, or cyclopentyl, unsubstituted or substituted by radicals from the group halogen and alkyl with 1 to 4 carbon atoms or furyl, or tetrahydrofuryl;

R3means a radical of the formula-N(B1-D1)(B2-D2where1In2D1and D2have the meanings given below;

R4means a radical of the formula-B3-D3and In3and D3have the meanings given below;

And1means direct alkylen with 1-5 carbon atoms or a straight albaniles with 2-5 carbon atoms;

And2means direct connection or direct alkylen with 1-4 carbon atoms;

In1In2and3independently denote a direct bond;

D1D2and D3independently mean hydrogen;

(X)nn denotes the number of the substituents X, while X means independently halogen, nitro or alkyl with 1-6 carbon atoms, unsubstituted or substituted by one or more radicals from the group halogen and alkoxy with 1-6 carbon atoms;

n is 0, 1 or 2,

moreover, the total sum of carbon atoms in the radicals And1and2-R2is at least 6 at the MOU carbon.

2. Derivatives of 2-amino-1,3,5-triazine of the formula (I) according to claim 1, wherein R3means a radical of the formula N(B1-D1)(B2-D2); R4means a radical of the formula - In3-D3;1means direct alkylen with 1-5 carbon atoms; And2means a direct bond or a group-CH2- ;1In2and3independently mean a direct link; D1D2and D3independently mean hydrogen; (X)nn denotes the number of the substituents X, while X means independently halogen or alkyl with 1-4 carbon atoms, unsubstituted or substituted by one or more radicals from the group halogen, alkoxy with 1-4 carbon atoms; n is 0, 1 or 2.

3. Derivatives of 2-amino-1,3,5-triazine of the formula (I) according to claim 1 or 2, wherein A1means a radical of the formula-CH2-, -CH2CH2-, -CH2CH2CH2or-CH2CH2CH2CH2andAnd2means a direct bond or a group of formula-CH2-and the number of carbon atoms of the sum of the carbon atoms of both radicals And1and A2- R2is 6-14 carbon atoms.

4. Derivatives of 2-amino-1,3,5-triazine of the formula (I) according to any one of claims 1 to 3, wherein A1means a radical of the formula-CH2CH2and And2has visari is the entered values and the number of carbon atoms of the sum of the carbon atoms of both radicals And 1and2- R26-8 carbon atoms.

5. Derivatives of 2-amino-1,3,5-triazine of the formula (I) according to any one of claims 1 to 3, wherein A1means a radical of the formula-CH2CH2CH2and And2has the above values and the number of carbon atoms of the sum of the carbon atoms of both radicals And1and A2- R26-8 carbon atoms.

6. Herbicide agent, characterized in that it contains a compound of the formula (I) according to one of claims 1 to 5 and additives customary in crop protection.

7. Method of pest plants, wherein an effective amount of the compounds of formula (I) according to one of claims 1-5 process plant or seed surface.



 

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