1,3,5-triazine derivatives, herbicide composition containing the same and intermediates

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention relates to 1,3,5-triazines of general formula I

,

wherein F is C3-C6-cycloalkyl, substituted with C1-haloalkyl or CHR3R4 wherein R3 and R4 are independently C1-C6-alkyl and C3-C6-cycloalkyl, and total amount of carbon atoms in R3 and R4 is 4 or more; R1 is amino, formylamino (C1-C4-alkyl)carbonylamino; R2 isC1-C4-haloalkyl. Also disclosed are intermediates and herbicide composition based on said 1,3,5-triazines.

EFFECT: compounds with high herbicidal activity.

7 cl, 10 tbl, 13 ex

 

The present invention relates to new nitrogen-containing 6-membered heterocyclic compounds with biological activity, and more particularly to derivatives of 1,3,5-triazine, herbicide compositions on their basis and intermediate connections.

Some of substituted 1,3,5-triazine with herbicide action already described (see Japanese patent application JP-A 19400/1961, U.S. patent US-A 3816419, U.S. patent US-A 3932167, Japanese patent application JP-A 192873/1983, international application WO-A 90/09378). Compounds (R)-6-chloro-N-(1-cyclohexylethyl)-N’-ethyl-1,3,5-triazine-2,4-diamine, (S)-6-chloro-N-(1-cyclohexylethyl)-N’-ethyl-1,3,5-triazine-2,4-diamine and (R,S)-6-chloro-N-(1-cyclohexylethyl)-N’-ethyl-1,3,5-triazine-2,4-diamine already described in the literature as herbicide active compounds (see source Z.Naturforsch., C; Biosc. (1987), 42, 663-669 specified in Chem. Abstracts 107:91770). However, to date, these compounds have not acquired a special significance.

The task of the invention to provide new derivatives of 1,3,5-triazines with high herbicide activity.

The problem is solved proposed derivatives of 1,3,5-trazine General formula (I)

in which a represents cycloalkyl with 3-6 carbon atoms, substituted C1-halogenation, or group R3R4in which R3and R4at the same time or Nezavisimaja from each other represent alkyl with 1-4 carbon atoms and cycloalkyl with 3-6 carbon atoms, the total number of carbon atoms of R3and R4is more than 3,

R1represents amino, formylamino, alkylcarboxylic with 1-6 carbon atoms in the alkyl group and

R2is halogenated with 1-4 carbon atoms in the alkyl group.

Preferred derivatives of 1,3,5-triazine are compounds that have

But is cyclohexyl, substituted C1-halogenation, or group CHR3R4in which R3and R4independently represents ISO-propyl, sec-butyl and cyclohexyl,

R1represents amino, formylamino, acetylamino, propionamido,

R2represents methyl, ethyl, ISO-propyl, substituted by fluorine, chlorine.

Preferred derivatives of 1,3,5-triazine are compounds that have

A is cyclohexyl substituted by trifluoromethyl or a group CHR3R4in which R3and R4independently represent ethyl, isopropyl and cyclohexyl,

R1represents amino, formylamino, acetylamino, propionamido,

R2represents methyl, ethyl, ISO-propyl, substituted by fluorine, chlorine.

The most preferred derivatives of 1,3,5-triazine are compounds that have

And is substituted by trifluoromethyl cyclohexyl or a group CHR3R4in which R3and R4/sup> independently represent methyl, ethyl and cyclohexyl,

R1represents amino, formylamino, ethylcarbodiimide or methylcobalamine,

R2is 1-foretel, diperchlorate, dichloromethyl or 1-fluoro-1-methylethyl.

An additional object of the invention is a herbicide composition which contains a compound of General formula (I) and conventional fillers and/or surfactants.

Compounds of General formula (I) in accordance with this invention contain at least one asymmetrically substituted carbon atom and therefore they can exist in different enantiomeric (R - and S-configurations) or diastereomeric forms. This invention relates as to the various possible individual enantiomeric or stereoisomeric forms of the General formula (I), and mixtures of these isomers.

New substituted 1,3,5-triazine General formula (I) receive, when

(a)

the biguanides of the General formula (II)

in which a and R1such as defined above,

- and/or acid adducts of compounds of General formula (II)

interact with alkoxycarbonyl compounds of General formula (III)

in which R2such as defined above, and

R5represents alkyl,

when the need is and in the presence of an excipient and diluent, and, if necessary, the obtained compound of General formula (I) is subjected to further transformation within the definition of the substituents, the usual methods

or (b)

1,3,5-triazine formula (la)in which R1is amino,

where a and R2such as defined above,

interact with the carbonyl-halogenides of the General formula (IV)

where R6represents formyl or alkylsulphonyl with 1 to 6 carbon atoms in the alkyl group and X2represents chlorine or bromine,

in the presence of a diluent and optionally in the presence of a base,

or (C)

compounds of General formula (Ia)in which R1is amino,

interact with carboxylic anhydrides of General formula (V)

where R6such as defined above,

in the presence of a diluent and optionally in the presence of a base,

or (d)

compounds of General formula (Ia)in which R1is amino,

interact with esters of carboxylic acids of General formula (VI)

where R5and R6such as defined above,

in the presence of a diluent and optionally in the presence of a base,

or (e

compounds of General formula (Ia)in which R1is amino,

interact with carboxylic acids of General formula (VII)

where R6such as defined above,

in the presence of a diluent and optionally in the presence of a condensing agent.

When using, for example, 1-(1-cyclohexylethyl)biguanide and complex methyl ester triperoxonane acid as starting materials, the reaction according to method (a) can be illustrated by the following scheme:

When using chloroethanol adduct 1-(1-ethylpropyl)biguanide and complex meteorologi ether 1-fluoro-1-metrokane acid as starting materials, the reaction according to method (a) can be illustrated by the following scheme:

When using, for example, N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine and acetylchloride as starting materials, the reaction according to method (b) can be illustrated by the following scheme:

When using, for example, N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine and acetic anhydride as starting materials, the reaction according to method (C) can be illustrated by the following scheme:

If IP is the use, for example, N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine and ethyl acetate as starting materials, the reaction according to method (d) can be illustrated by the following scheme:

When using, for example, N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine and acetic acid as starting materials, the reaction according to method (e) can be illustrated by the following scheme:

Suitable acid adducts of compounds of the formula (II) represent addition products with proton acids such as, for example, with hydrogen chloride, bromoiodide, sulfuric acid, methanesulfonate, benzosulfimide and p-toluensulfonate.

Starting materials of General formula (II) is still not yet described in the literature; as new compounds, they also constitute an additional object of the present invention.

New biguanides of the General formula (II) are obtained when substituted amines of General formula (VIII)

where As the same as defined above,

and/or acid adducts of compounds of General formula (VIII), such as, for example, hydrochloride interact with cyanoguanidine (“dicyandiamide”) of the formula (IX)

if necessary, in the presence of an auxiliary with the organisations, such as, for example, hydrogen chloride, and optionally in the presence of a diluent, such as, for example, n-decane or 1,2-dichlorobenzene, at temperatures from 100 to 200°With (see receipt).

After receiving the biguanides of the General formula (II) can be used directly, without intermediate isolation, to obtain the compounds of General formula (I) according to the above methods.

Examples of hydrochloride compounds of General formula (II) according commissioned by the invention include 1-methylbutylamine hydrochloride, 1,2-dimethylpropylene hydrochloride, 1,3-dimethylbiguanide hydrochloride, 1-ethylpropylamine hydrochloride, 1-ethylbutylamine hydrochloride, 1-ethyl-2-methylpropylamine hydrochloride, 1-ethylpentane hydrochloride, 1-ethyl-2-methylbutylamine hydrochloride, 1-ethyl-3-methylbutylamine hydrochloride, 1-ethyl-2,2-dimethylpropylene hydrochloride, 1-cyclopropanecarboxamide hydrochloride, 1-cyclopentylpropionic hydrochloride, 1-cyclohexylpropionic hydrochloride, 1-propylethylene hydrochloride, 1-isopropyltoluene hydrochloride, 1-Propylenediamine hydrochloride, 1-isopropyl-2-methylpropylamine hydrochloride, 1-isopropylbenzylamine hydrochloride, 1-butylaniline hydrochloride, 1-isobutylbarbituric hydrochloride, 1,5-dimethylhexylamine hydrochloride, 1-pentile illigant hydrochloride, 1-ethyl-3-forprofessional hydrochloride, 3-chloro-1-ethylpropylamine hydrochloride, 1-ethyl-2-forprofessional hydrochloride, 1-ethyl-4-terbutaline hydrochloride, 4-chloro-1-ethylbutylamine hydrochloride, 2-triftormetilfullerenov hydrochloride, 3-triftormetilfullerenov hydrochloride, 4-triftormetilfullerenov hydrochloride, 1,1-dimethyl-2-propenylboronic hydrochloride, 1-cyano-1-methylethylamine hydrochloride and so on.

Substituted amines of General formula (VIII)required as precursors are known and/or can be obtained by methods known from the literature (see Bull. Soc. Chim. France 1952, 276-279; Ogre. link 1953, 974-981; Bull. Chem. Soc. Japan 57 (1984), 1570-1575; J. Am. Chem. Soc. 76(1954), 4564-4570; Ogre. link 80 (1958), 5270-5272, JIKKEN DEPENDING KOUZA (Lectures of experimental chemistry), published by the Chemical Society of Japan, vol. 14, str (1978), published by Maruzen; J. Am. Chem. Soc., 75, 3212 (1953); J. Am. Chem. Soc., 78, 860 (1956); J. Am. Chem. Soc., 66, 1517 (1944); Angew. Chem. Int. Ed., 7, 919 (1968); J. Chem. Soc., 2348 (1926); Synthesis, 717 (1980); Org. React., 3, 267 (1946); J. Chem. Soc., 267 (1941); Org. React, 3, 307 (1946); Org. React, 3, 337 (1946); J. Org. Chem. USSR, 16, 1031 (1980); Farmaco Ed. Sci., 22, 1037 (1967); J. Biol. Chem., 120, 772 (1937); international application WO 92/12121; European patent application EP-A 176327; CS-B233428; German patent application DE-A 2843480 and so on).

Examples of hydrochloride compounds of General formula (VIII) in accordance with this invention are 1-methylbutylamine hydrochloride, 1,2-dimethylpropylene hydrochloride, 1,3-is emotivational hydrochloride, 1-ethylpropylamine hydrochloride, 1-ethylbutylamine hydrochloride, 1-ethyl-2-methylpropylamine hydrochloride, 1-ethylphenethylamine hydrochloride, 1-ethyl-2-methylbutylamine hydrochloride, 1-ethyl-3-methylbutylamine hydrochloride, 1-ethyl-1,1-dimethylpropylene hydrochloride, 1-cyclopropylamine hydrochloride, 1-cyclopentylpropionyl hydrochloride, 1-cyclohexylpropionic hydrochloride, 1-propylethylene hydrochloride, 1-isopropylbenzylamine hydrochloride, 1-propylpentyl hydrochloride, 1-isopropyl-2-methylpropylamine hydrochloride, 1-propylpentyl hydrochloride, 1-isopropyl-2-methylpropylamine hydrochloride, 1-isopropylbenzylamine hydrochloride, 1-butylmethylamine hydrochloride, 1-isobutylparaben hydrochloride, 1,5-dimethylhexylamine hydrochloride, 1-pentylhexyl hydrochloride, 1-ethyl-3-forprofile hydrochloride, 3-chloro-1-ethylpropylamine hydrochloride, 1-ethyl-2-forprofile hydrochloride, 1-ethyl-4-terbutalin hydrochloride, 4-chloro-1-ethylbutylamine hydrochloride, 2-triftormetilfullerenov hydrochloride, 3-triftormetilfullerenov hydrochloride, 4-triftormetilfullerenov hydrochloride, 1,1-dimethyl-2-Propylamine hydrochloride, 1-cyano-1-methylethylamine hydrochloride and so on.

The compounds of formula (IX) are synthetic compounds known in organic chemistry.

Formula (III) provides a General definition alkoxycarbonyl compounds, and is used below as the starting compounds in the method in accordance with this invention to produce compounds of General formula (I). In the General formula (III), R2preferably or particularly preferably has the value stated above in the description of the compounds of General formula (I) in accordance with this invention as preferred or particularly preferred for R2. R5preferably is an alkyl having from 1 to 4 carbon atoms, in particular stands or ethyl.

Starting materials of General formula (III) are known chemicals for synthesis (see, for example, German patent application DE-A 4131242, European patent application EP-A 850911, EP-A 468681, Japanese patent application JP-A 301844/1993, J. Org. Chem., 33, 4279 (1968), and so on). Examples of such compounds are methyl-1-forproposal, ethyl-1-forproposal, propyl-1-forproposal, butyl-1-forproposal, methyl-1-fluoro-1-methylpropionate, ethyl-1-fluoro-1-methylpropionate, propyl-1-fluoro-1-methylpropionate, butyl-1-fluoro-1-methylpropionate and so on.

Compounds of General formula (la), which are used as starting compounds in the methods (b), (C), (a) and (e) are new and can be obtained, for example, in the form of a subgroup of compounds of formula (I) according to the method (a). Examples of such compounds are N-(1-methylbutyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, N-(1,2-dimethylpropyl)-6-(1-foradil)-1,3,5-triazine-2,4-diamine, N-(1,3-dimethylbutyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-di is min, N-(1,5-diethylhexyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, N-(1-ethylpropyl)-6-(1-foradil)-1,3,5-triazine-2,4-diamine, N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, N-(1-ethylbutyl)-6-(1-foradil)-1,3,5-triazine-2,4-diamine, N-(1-ethylbutyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, N-(1-ethyl-2-methylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, N-(1-ethylphenyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, and so on.

Compounds of formula (IV), (V), (VI) and (VII) are known synthetic compounds of organic chemistry. In these compounds R6preferably is formyl, ethylcarbonate, methylcarbamyl.

Examples of compounds of General formula (IV) are acetylchloride, acetylmuramic, propionitrile.

Examples of compounds of General formula (V) are acetic anhydride and propionic anhydride.

Examples of compounds of General formula (VI) are methylformate, ethyl formate, n-paperformat, n-bodyformat, methyl acetate, ethyl acetate, n-propyl, n-butyl acetate, methylpropionate, ethylpropyl, n-propylbromide and n-butylbromide.

Examples of compounds of General formula (VII) are formic acid, acetic acid and propionic acid.

The method of obtaining compounds of General formula (I) according to the method (a) is preferably carried out using a diluent. Suitable diluents include, in opalanie to water, preferably organic solvents. They include, in particular, aliphatic, alicyclic or aromatic, optionally halogenoalkane, hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, disutility ether, dioxane, dimethoxymethane (DMM), tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, methyl ethyl ketone (MEK), butanone, methylisobutylketone or methyl isobutyl ketone; NITRILES, such as acetonitrile propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, sulfoxidov, such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n - or isopropanol, butanol, ethylene glycol, ethylene glycol onomatology ether, ethylene glycol monotropy ether, diethylene glycol onomatology ether, diethylene monotropy ether, mixtures thereof with water or distilled water.

Suitable auxiliary connection for the reactions according to the method (a) are, in General, conventional inorganic or organic is their bases or acid acceptors. They preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides of alkali or alkaline earth metals, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, methoxide, ethoxide, n - or ISO-propoxy, n-, ISO-, sec - or tert-piperonyl sodium, or methoxide, ethoxide, n - or ISO-propoxy, n-, ISO-, sec - or tert-piperonyl potassium; in addition, basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, Tripropylamine, tributylamine, ethyldiethanolamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldiglycol, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl-and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridin, 1,1,4,4-tetramethylethylenediamine (TMEDA), 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as well as organolithium compounds, such as, for example, IU illite, n-utility, second-utility, tert-utility, finality, sitedisability, n-utility * DABCO, n-utility * DBN, n-utility * TMEDA and so on.

When carrying out process (a) the reaction temperature can vary in a relatively wide range. In General, the process is carried out at a temperature from 0 to 150°C, preferably from 10 to 120°C.

The reaction is usually carried out at atmospheric pressure. However, it is also possible to conduct the reaction at elevated or reduced pressure, typically from 0.1 to 10 bar.

For carrying out process (a) the parent compound is usually used in equimolar amounts, 1 mol of the compounds of General formula (II) may communicate, for example, with 1-2 moles of the compounds of General formula (III) in the presence of a base, for example, 1-2 moles of ethoxide sodium in diluent ethanol. However, it is also possible to use a relatively large excess of one of the components. The reaction is usually carried out in a suitable diluent in the presence of an ancillary compound and the reaction mixture is typically stirred at the required temperature for several hours. The treatment is carried out by conventional methods (see receipt).

Methods (a), (b), (C), (d) and (e) is preferably carried out with the use of risalites. Suitable diluents for carrying out the process in accordance with the data and the acquisition include, in addition to water, preferably inert organic solvents. These solvents include, in particular, aliphatic, alicyclic or aromatic, optionally halogenoalkane, hydrocarbons, such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride; ethers, such as diethyl ether, metaliteracy ether, diisopropyl ether, disutility ether, dioxane, dimethoxymethane (DMM), tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, methyl ethyl ketone (MEK), Bhutan, methylisobutylketone or methyl isobutyl ketone; NITRILES, such as acetonitrile, propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, sulfoxidov, such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n - or ISO-propanol, butanol, ethylene glycol, ethylene glycol onomatology ether, ethylene glycol monotropy ether, diethylene glycol onomatology ether, diethylene monotropy ether, mixtures thereof with water or distilled water.

Suitable auxiliary connection for the implementation of the methods (a), (b), (C) or (d) represents the t a, in General, the usual inorganic or organic bases or acid acceptors. They preferably include acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides of alkali or alkaline earth metals, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, methoxide, ethoxide, n - or ISO-propoxy, n-, ISO-, sec - or tert-piperonyl sodium, or methoxide, ethoxide, n - or ISO-propoxy, n-, ISO-, sec - or tert-piperonyl potassium; in addition, basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, Tripropylamine, tributylamine, ethyldiethanolamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldiglycol, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl - and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridin, 1,1,4,4-tetramethylethylenediamine (TMEDA), 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-disabili the lo[5.4.0]undec-7-ene (DBU).

Method (e) is preferably carried out in the presence of a condensing agent. Examples of such condensing agents include dicyclohexylcarbodiimide, acetic anhydride, thionyl chloride, pentachloride phosphorus oxychloride phosphorus, aluminum oxide, silicon tetrachloride, titanium tetrachloride and so on.

When carrying out processes (b), (C), (d) or (e) the reaction temperature may vary within relatively wide limits. In General, the process is carried out at a temperature from 0 to 150°C, preferably from 0 to 120°C.

The reaction is usually carried out at atmospheric pressure. However, it is also possible to carry out the process in accordance with this invention at elevated or reduced pressure, typically from 0.1 to 10 bar.

For carrying out process (b) the parent compound is usually used in equimolar amounts, 1 mol of the compounds of General formula (Ia) may communicate, for example, from 0.8 to 2.0 moles of the compounds of General formula (IV) in the presence of a base, for example 1-3 moles of triethylamine. However, it is also possible to use a relatively large excess of one of the components.

For carrying out process (C) the parent compound is usually used in equimolar amounts, 1 mol of the compounds of General formula (la) may communicate, for example, from 0.8 to 2.0 moles of the compounds of General formula (V) in the presence of a base, for example 1-3 moles of triethyl is in. However, it is also possible to use a relatively large excess of one of the components.

For carrying out process (d) the parent compound is usually used in equimolar amounts, 1 mol of the compounds of General formula (Ia) may communicate, for example, from 0.8 to 2.0 moles of the compounds of General formula (VI) in the presence of a base, for example 1-3 moles of sodium methoxide. However, it is also possible to use a relatively large excess of one of the components.

For carrying out process (e) the parent compound is usually used in equimolar amounts, 1 mol of the compounds of General formula (Ia) may communicate, for example, from 0.8 to 2.0 moles of the compounds of General formula (IV) in the presence of a condensing agent, such as dicyclohexylcarbodiimide. However, it is also possible to use a relatively large excess of one of the components.

Active compounds in accordance with this invention are particularly suitable for use as a defoliant, drying means, destroyers tops and especially herbicides. Under the weeds, in the broadest sense, refers to all the plants that grow in areas where they are unwanted. Are there connections in accordance with this invention as total or selective herbicides depends mainly on the quantities used. Active connections according to the accordance with this invention can be used, for example, for the following plants.

Dicotyledonous weeds of the genus: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledonous crops of the genus: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genus: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilop, Phalaris.

Monocotyledonous crops of the genus: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of active compounds in accordance with this invention is in no way restricted to these genera, but also extends in the same manner to other plants.

When using these forms of active compounds in accordance with this invention can also be used in transgenic plants. In this case, you get a synergistic effect.

Active compounds in accordance with this invention are suitable, depending on the concentration, for full control growth of weeds, for example, in industrial areas or jelly is accessible ways, on the tracks or squares with or without tree planting. Equally active compounds in accordance with this invention can be used to control the growth of weeds in perennial cultures, for example, stands, decorative plantings of trees, orchards, vineyards, plantations of citrus, nut trees, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, plantations of coconut trees, the planting of juicy fruit and hops, on lawns, turf and pasture, and for selective weed control in annual crops.

The compounds of formula (I) in accordance with this invention have a strong herbicide action and broad spectrum of activity when applied to the soil and aboveground parts of plants. To a certain extent they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds, in particular monocotyledonous crops, both before and after germination.

The active compounds can be converted into conventional preparative forms such as solutions, emulsions, wettable powders, suspensions, powders, dusty, pastes, soluble powders, granules, concentrated suspensions and emulsions, natural and synthetic materials impregnated with active is an Association, and micro-capsules in polymeric substances.

These formulations of get known methods, for example, by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam.

In the case of using water as a filler as auxiliary solvents can also be used, for example, organic solvents. Suitable liquid solvents are aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example fractions of mineral or vegetable oils, alcohols, such as butanol or glycol, and also ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water.

Suitable solid carriers are, for example, ammonium salts and natural ground minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmor lonit or diatomaceous earth, and crushed synthetic minerals such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, thick and dolomite, and synthetic granules of inorganic and organic stone flour, and granules of organic material such as sawdust, coconut shell, corn and tobacco stems; suitable emulsifiers and/or foaming agents are, for example, nonionic and anionic emulsifiers, such as esters of polyoxyethylene fatty acid ethers, polyoxyethylene fatty alcohol, for example alkylarylsulphonate ethers, alkyl sulphonates, alkyl sulphates, arylsulfonate and protein hydrolysates; suitable dispersing agents are, for example, ligninsulfonate liquid waste and methylcellulose.

Thickeners, such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules, or matrix, such as gum Arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as capalini and lecitine, and synthetic phospholipids, can be used in the formulation. Other additives can be mineral and vegetable oils.

You can use the SQL dyes, such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic dyestuffs, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparative forms usually contain from 0.1 to 95 wt.% active compounds, preferably from 0.5 to 90 wt.%.

To control growth of weeds active connection in accordance with this invention, as such or in the form of a formulation, can also be used in a mixture with known herbicides, possible a ready mix or a tank mix.

Examples of known herbicides that are suitable for mixtures include acetochlor, acifluorfen(-sodium), klonipin, alachlor, aloxide(-sodium), ametrine is high, amithlon, amidosulfuron, anilofos, Azul, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), belforest, encultured(-methyl), bentazon, benzamycin, benzefoam, benzoylperoxy(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutyl, bromophenoxy, bromoxynil, butachlor, butoxide, butyl, cafestol, galaxidi, carbetamide, Capistrano(-ethyl), chlorethoxyfos, chloramben, ozone chloride, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlorotoluron, cinidon(-ethyl), cinmetacin, chinaculture, klavox is dim, clethodim, clodinafop(-propargyl), clomazone, clomipram, clopyralid, cloperastine(-methyl), karasulu(-methyl), cumyluron, cyanazine, cybotron, cycloate, cycloaliphatic, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), dicloflam, diacetyl(-ethyl), difenzoquat, diflufenican, diflubenzuron, dimefuron, timepart, dimethachlor, deltamethrin, dimethenamid, Dimexidum, dinitramine, diphenamid, Diquat, dithiopyr, Diuron, damron, aprobada, ARTS, asbroker, ethalfluralin, atomiculture(-methyl), ethofumesate, idoxifene, ethoxysulfuron, etamesonic, fenoxaprop(-P-ethyl), phentramin, planrep(-isopropyl), planrep(-isopropyl-L), planrep(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), flatlet, flucarbazone, flufenacet, flumetsulam, flumiclorac(pencil), flumioxazin, flubiprofen, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flourophenyl, fluspirilene(-methyl-sodium), flurenol(-butyl), fluridone, fluroxypyr(-methyl), flurried, flurtamone, fluthiacet(-methyl), flutamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), galasoft, haloxyfop(ethoxyethyl), haloxyfop(P-methyl), hexazinone, imazamethabenz(-methyl), imazethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -soda is th), ioxynil, isopropylene, Isoproturon, Sauron, isoxaben, isoxaflutole, isoxaflutole, isocaporate, lactofen, lenacil, linuron, MSRA, MSRB, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metaventure, metobromuron, (alpha)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinet, monolinuron, nitroanilide, napropamide, neburon, nicosulfuron, norflurazon, arrancars, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxacyclobutane, oxyfluorfen, paraquat, pelargonia acid, pendimethalin, pentalyn, phenoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, prophetarum, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), paradoxien, perbenzoic, perimutter, peridot, Perminova(-methyl), pyrithiobac(-sodium), chinkara, hinnerk, hinkleman, hisamoto(-P-ethyl), hisamoto(-R-tefuryl), rimsulfuron, sethoxydim, Simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate sulfosulfuron, tabulam, tebuthiuron, tepraloxydim, terbutylazine, terbutryn, tanishlar, tefloned, thiazopyr, thidiazuron, thifensulfuron(-methyl), thiobencarb, thiocarbonyl, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl), triclopyr, tridiphane, trifluralin and triple Ulthuan.

It is also possible mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, means to scare away birds, nutrients for plants and soil conditioner.

To improve compatibility with agricultural crops is also possible to mix the compounds of General formula (I) with one or more protecting agents, for example protecting agent is 1-(α,α-dimethylbenzyl)-3-p-trilocana.

The active compounds can be applied as such, in the form of preparative forms or in forms made of them by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are made by usual methods, for example by watering, spraying, raspryskivanii, scattering.

Active compounds in accordance with this invention can be applied either before or after germination. They can also be introduced into the soil before planting.

The applied amount of active compounds can vary considerably. Basically it depends on the nature of the desired effect. Usually the usage rate is from 1 g to 10 kg of active compound per hectare of soil surface, preferably from 5 g to 5 kg per 1 hectare

Receipt and use of the active compounds in accordance with the laws the AI with this invention is described using the following examples.

Example 1

At room temperature (approximately 20° (C) a solution of 4.7 g (85 mmol) of sodium methoxide in 100 ml of methanol is added under stirring to a mixture of 20 g (80 mmol) of the hydrochloride of (R,S)-1-cyclohexylethylamine, 10 g (80 mmol) of methyl 2-forproperty and 100 ml of methanol and the reaction mixture was stirred at room temperature for 15 hours. After concentration in vacuo, the generated water pump, the residue is shaken with methylene chloride and water and the organic phase is dried over sodium sulfate and filtered. The solvent is carefully distilled off under reduced pressure from the filtrate.

Gain of 9.2 g (43% of theoretical) of (R,S)-N’-(1-cyclohexylethyl)-6-(1-foradil)-1,3,5-triazine-2,4-diamine as an amorphous residue.

logP=1,83a).

Example 2

A mixture of 3.5 g (13 mmol) of (R,S)-N’-(1-cyclohexylethyl)-6-(1-foradil)-1,3,5-triazine-2,4-diamine (example 1) and 25 ml of propionic anhydride is stirred at a temperature of 130°C for 60 minutes. Volatile components are then carefully distilled off under reduced pressure.

Obtain 3.8 g (90% of theoretical) of (R,S)-N-[4-(1-cyclohexylethylamine)-6-(1-foradil)-1,3,5-triazine-2-yl]propionamide in the form of an amorphous residue.

logP=3,14a).

Example 3

A mixture of 3.5 g (13 mmol) of (R,S)-N’-(1-cyclohexylethyl is)-6-(1-foradil)-1,3,5-triazine-2,4-diamine (example 1), 2.5 g (21 mmol) of N,N-dimethylformamidine and 50 ml of 1,4-dioxane was stirred at room temperature (approximately 20°C) for 15 hours. After adding 80 ml of water and 3 ml of concentrated hydrochloric acid the mixture is stirred at room temperature for another 60 minutes. The crystalline product is then allocate filtration with suction.

Obtain 1.8 g (47% of theoretical) of (R,S)-N-[4-(1-cyclohexylethylamine)-6-(1-foradil)-1,3,5-triazine-2-yl]-formamide with a melting point 127°C.

logP=3.04 froma).

Example 4

4.94 g of the hydrochloride of ethylpropylamine suspended in 50 ml of 1,2-dichlorobenzene. Add to 3.36 g of cyanoguanidine and the mixture is then stirred at a temperature of from 150 to 170°C for 3 hours. The crystalline product is further isolated by filtration with suction and washed three times with simple ether (10 ml). Fraction of volatile solvent is then carefully distilled off under reduced pressure to get ethylpropylamine, which is used for subsequent reactions without further purification.

Next, 1.10 g of metallic sodium is mixed with 150 g of methanol. After the sodium will react completely, to the mixture of 5.29 g ethylpropylamine and the mixture is stirred at room temperature for 48 hours. Volatile methanol is then distilled off under reduced Yes the tion. The solid residue is mixed with 80 ml of water and the mixture extracted with ethyl acetate (120 ml). The organic phase is dried over anhydrous sodium sulfate and the solvent is distilled off under reduced pressure. Purification by chromatography on a column of silica gel (mobile phase: a simple ether/n-hexane = 1:1) gives the desired product.

Get 3,20 g (33% of theoretical) of N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine with a melting point 104-106°C.

Example 5

1 g of N-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine and 5.63 g of triethylamine are suspended in 30 ml of tetrahydrofuran. When the temperature is 5°add 3,39 g acetylchloride and the mixture is heated under reflux for 2 hours. The reaction mixture was mixed with 60 ml of saturated sodium bicarbonate solution and extracted with 80 ml of ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate to obtain the crude product, after purification by chromatography on a column of silica gel (mobile phase: a simple ether/n-hexane = 1:1) gives the desired product.

With almost quantitative yield gain of 1.17 g of N-acetyl-N’-(1-ethylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine with a melting point 109-111°C.

Similar to the methods of examples 1-5 and in accordance with the General description of the process of obtaining, in accordance with this from what rutenium it is also possible to obtain, for example, compounds of General formula (I)shown in table 1 below.

Table 1

Examples of compounds of formula (I)
Ave. No.AndR1R2Physical and stereochemical data
6NH2CF2CllogP=3,51a)

(racemate)
7NH2CF(CH3)2logP=1,93a)

(racemate)
8CF2CllogP=4,23a)

(racemate)
9CF(CH3)2logP=3,30a)

(racemate)
10F3logP=3.04 froma)

(racemate)
11 CF(CH3)2logP=3,44a)

(racemate)
12NH2F3logP=1,83a)

(R enantiomer)

Table 1 (continued)
Ave. No.AndR1R2Physical and stereochemical data
13NH2CF(CH3)2log=1,93a)

(R enantiomer)
14NH2CHCl2log=3,21a)

(R enantiomer)
15F3logP=3,11a)

(R enantiomer)
16CF(CH3)2logP=3,25a)

(R enantiomer)
17 CHCl2logP=2,93a)

(R enantiomer)
18NH2CHFCH3logP=1,82a)

(S enantiomer)
19NH2CF(CH3)2logP=1,92a)

(S enantiomer)

Table 1 (continued)
Ave. No.AndR1R2Physical and stereochemical data
20NH2CHCl2logP=3,20a)

(S enantiomer)
21CHFCH2logP=3,11a)

(S enantiomer)
22CF(CH3)2logP=3,26a)

(S enantiomer)
23CHCl2 logP=2,93a)

(S enantiomer)
24NH2F3logP=2,05a)

(R enantiomer)
25NH2CF(CH3)2logP=2,13a)

(R enantiomer)
26NH2CHFCH3logP=2,05a)

(S enantiomer)

td align="center"> 30
Table 1 (continued)
Ave. No.AndR1R2Physical and stereochemical data
27NH2CF(CH3)2logP=2,12a)

(S enantiomer)
28CH3CH2CH2CH(CH3)NH2(CH3)2CFTPL 108-111°

(racemate)
29(CH3)2SNSN2CH(CH3)NH2CH3Fn20D1,51590

(racemate)
(CH3)2SNSN2CH(CH2)NH2(CH3)2CFTPL 123-125°

(racemate)
31(CH3)2CHCH2CH2CH2CH(CH3)NH2(CH3)2CFTPL 107-110°

(racemate)
32(C2H5)CH(C2H5)NH2CH3FTPL 89-90°

(racemate)
33(C2H5)CH(C2H5)NH2(CH3)2CFTPL 104-106°

(racemate)
34(C2H5)CH(C2H5)NHCOCH3(CH3)2CFTPL 109-111°

(racemate)
35NH2(CH3)2CFn20D1,4780

(racemate)

The logP values given in table 1, determined according to EEC Directive 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) on a column of reverse phase (C 18). Temperature 43°C.

(a) the Mobile phase for the determination in the acidic range: 0.1% aqueous fo what FORNEY acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - the corresponding data in table 1 are markeda).

The calibration is carried using unbranched Alkan-2-ones (having from 6 to 16 carbon atoms) with known logP values (logP values determined using the retention time through linear interpolation between the two following each other by alkenone).

The values of lambda max is determined using the UV range from 200 to 400 nm at the maximum of the chromatographic signals.

Starting materials of the formula (II)

Example (II-1)

A mixture of 28.4 g (0.4 mol) of (R,S)-1-cyclohexylethylamine, 350 ml of toluene, 150 ml of decane and 48 g of 30% strong aqueous hydrochloric acid is subjected to azeotropic distillation. The liquid is distilled until then, until it reaches an internal temperature of 135°C. At this temperature, the remaining mixture of 33.6 g (0.4 mol) of cyanoguanidine and the reaction mixture is stirred at a temperature of 135°C for 2 hours. The mixture is cooled to room temperature, add about 100 ml of acetone and the crystalline product are filtered with suction.

Get to 67.9 g (69% of theoretical) of hydrochloride (R,S)-1-cyclohexyl-acid-biguanide in the form of a solid product.

Similarly to the method of example II-1 it is also possible to obtain, for example, with the organisations of General formula (II), presented in table 2 below.

Table 2

Examples of compounds of the formula (II). In each case, these compounds are hydrochloride.
Ave. No.AndR1Stereochemical data
II-2NH2(R enantiomer)
II-3NH2(S enantiomer)
II-4NH2(R enantiomer)
II-5NH2(S enantiomer)

Examples confirming the biological activity of the compounds of formula (I)

Example a-1

Testing before germination

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 parts by weight of alkylarylsulphonates ether.

To obtain a suitable formulations of active compound, 1 parts by weight of active compound is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

The seeds of esterwegen plants are sown in normal soil. After ~24 hours on the ground razbryzgivayut preparative form of the active compound so that a certain desired amount of active compounds falling on unit area. The concentration of the liquid to raspryskivanii is that per hectare was applied a certain desired amount of active compound in 1000 litres of water.

After three weeks, the degree of plant damage estimate in % damage in comparison with the growth of the untreated plants.

Numbers mean:

0% = no action (as in the untreated control plants).

100% = total destruction.

In this test, for example, the compound of preparative example 1 exhibits strong activity against weeds, and at the same time well tolerated by crops, such as corn.

Example a-2

Testing before germination

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 parts by weight of benzyloxypropionic ether.

To obtain a suitable formulations of the active compounds 1 parts by weight specified in table a-2 active compound is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants (Echinocloa crus galli, Setaria viridus, Amaranthus lividus and Polygonum blumei MEISSN) are sown in ordinary the th soil. Soil razbryzgivayut preparative form of the active compound so that a certain desired amount of active compounds falling on unit area.

Through four weeks, the degree of plant damage estimate in % damage in comparison with the growth of the untreated plants.

Numbers mean:

0% = no action (as in the untreated control plants).

100% = total destruction.

The results of the experiment are summarized in table a-2.

Example-1

Testing after germination

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 parts by weight of alkylarylsulphonates ether.

To obtain a suitable formulations of the active compounds 1 parts by weight specified in table B-1-1 - 1-5 active compound is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

The test plants with a height of 5-15 cm are sprayed with the preparative form of the active compound so that a certain desired amount of active compounds falling on unit area. The concentration of the liquid to raspryskivanii so that a certain desired amount of active compound was applied in 1000 l/ha

After three weeks, the degree of plant damage estimate in % damage in comparison with croston untreated plants. Numbers mean:

0% = no action (as in the untreated control plants).

100% = total destruction.

The results of the experiment are summarized in tables B-1-1 - 1-5.

Example b-2

Testing after germination

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 parts by weight of benzyloxypropionic ether.

To obtain a suitable formulations of the active compounds 1 parts by weight specified in table b-2 active compound is mixed with the specified amount of solvent, add the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration.

Test plants (Echinocloa crus galli, Setaria viridus, Amaranthus lividus and Polygonum blumei MEISSN), which are on average in stage 2 of the sheet, sprayed preparative form of the active compound so that a certain desired amount of active compounds falling on unit area.

After three weeks, the degree of plant damage estimate in % damage in comparison with the growth of the untreated plants.

Numbers mean:

0% = no action (as in the untreated control plants).

100% = total destruction.

The results of the experiment are summarized in table b-2.

Table a-1

Testing before germination/greenhouse
The consumption rate g A.S./haCornAbutilonAmaranthus
    
(1)500080100
Table a-2

Pre-emergence treatment/greenhouse
The active compound example No.The consumption rate g A.S./haEchinochloa grus-galliAlopecurusAmaranthus lividus, LPolygonum blumei MEISSN
(32)1000>90>90>90>90
(33)1000>90>90>90>90
(34)1000>90 >90>90>90
(35)1000>90>90>90>90
Table b-1-1:

Testing after germination/greenhouse
The active compound example No.The consumption rate g A.S./haCornSetariaAmaranthusSinapis
     
(9)500309095100

 
Table b-1-2

Testing after germination/greenhouse
The active compound example No.The consumption rate g A.S./haSetariaAbutilonAmaranthusSinapis
    
(5)500959010095
     
(3)50010090100100

Table b-1-4

Testing after germination/greenhouse
The active compound example No.The consumption rate g A.S./haSetariaAmaranthusSinapisXanthium
     
(6)500100100100100
     
(2)500100100100100
Table b-1-5

Testing polypropalene/greenhouse
The active compound example No.The consumption rate g A.S./haSetariaAmaranthusSinapisXanthium
     
(7)500100100100100

Table b-1-5 finish
The active compound example No.The consumption rate g A.S./haSetariaAmaranthusSinapisXanthium
     
(8)500100100100100
Table b-2

Post-harvest handling/greenhouse
The active compound example No.The consumption rate g A.S./haAmaranthus lividus, L.Polygonum blumei MEISSN
(28) 1000100100
(29)1000100100
(31)1000100100
(35)1000100100

Examples preparative forms

Example formulation 1 (granules)

25 parts by weight of water is added to a mixture of 10 muscicapinae of example 28, 30 parts by weight of bentonite (montmorillonite), 58 parts by weight of talc and 2 parts by weight of ligninsulfonate salt. The components are thoroughly mixed with each other and used to produce extrusion granulator, the granules (particle size of 10-40 mesh), which are dried at a temperature of 40-50°C.

Example formulation 2 (emulsifiable concentrate)

30 parts by weight of the compound of example 32, 55 parts by weight of xylene, 8 parts by weight of polyoxyethyleneglycol ether and 7 parts by weight of Las calcium mix and while stirring, treated with obtaining emulsifiable concentrate.

Example formulation 3 (wettable powder)

15 parts by weight of the compound of example 33, 80 parts by weight of a mixture (5:1) “white soot” (fine particles gidrirovannoe amorphous duoci and silicon) and sprayed loam and 3 parts by weight of condensate of naphthalenesulfonate sodium/formalin are combined and mixed to obtain wettable powder.

The preparative example form 4 (wettable granules)

20 parts by weight of the compound of example 35, 30 parts by weight of lignosulfonate sodium, 15 parts by weight of bentonite and 35 parts by weight of calcined pulverized diatomaceous earth intensively mixed with water. The resulting product granularit extrusion through a 0.3 mm sieve. Drying gives wetted capsules.

1. Derivatives of 1,3,5-triazine of General formula (I)

in which

A represents cycloalkyl with 3-6 carbon atoms, substituted C1-halogenation, or group R3R4in which R3and R4at the same time or independently of one another represent alkyl with 1-6 carbon atoms and cycloalkyl with 3-6 carbon atoms, the total number of carbon atoms of R3and R4is more than 3,

R1represents amino, formylamino, alkylcarboxylic with 1-6 carbon atoms in the alkyl group,

R2is halogenated with 1-4 carbon atoms in the alkyl group.

2. Derivatives of 1,3,5-triazine according to claim 1, in which

But is cyclohexyl, substituted C1-halogenation, or group R3R4in which R3and R4independently represents an isopropyl, a is orbutil and cyclohexyl,

R1represents amino, formylamino, acetylamino, propionamido, R2represents methyl, ethyl, isopropyl, substituted by fluorine, chlorine.

3. Derivatives of 1,3,5-triazine according to claim 1, in which

A is cyclohexyl substituted by trifluoromethyl, or a group R3R4,in which R3and R4independently represent ethyl, isopropyl and cyclohexyl,

R1represents amino, formylamino, acetylamino, propionamido,

R2represents methyl, ethyl, isopropyl, substituted by fluorine, chlorine.

4. Derivatives of 1,3,5-triazine according to claim 1, in which

And is substituted by trifluoromethyl cyclohexyl, or a group R3R4in which R3and R4independently represent methyl, ethyl and cyclohexyl,

R1represents amino, formylamino, ethylcarbodiimide or methylcobalamine,

R2is 1-foretel, diperchlorate, dichloromethyl or 1-fluoro-1-methylethyl.

5. Compounds of General formula (II)

in which

A represents a group R3R4in which R3represents alkyl with 1-4 carbon atoms and R4is cycloalkyl with 3-6 carbon atoms,

R1represents amino, formylamino, alkylcarboxylic with 1-6 atoms the carbon in the alkyl group,

and their acid additive salt.

6. Compounds according to claim 5, in which

And represents the group in which R3R4in which R3represents alkyl with 1-4 carbon atoms and R4represents cyclohexyl.

7. Herbicide composition, characterized in that it contains a compound according to any one of claims 1 to 4 and conventional fillers and/or surfactants.

Priorities:

01.12.1998 connection, And which means cycloalkyl with 3-6 carbon atoms, substituted C1-halogenation, R1means amino, formylamino or alkylcarboxylic with 1-6 carbon atoms in the alkyl group, R2mean 1-fluoro-ethyl and 1-fluoro-1-methylethyl;

27.05.1999 connection, in which a represents a group R3R4in which one of the radicals R3and R4means alkyl with 1-4 carbon atoms, and the other is cyclohexyl, R2means alkyl with 1-4 carbon atoms, substituted with halogen, in addition to the above groups;

On 25.11.1999 connection, in which a represents a group R3R4in which R3and R4at the same time or independently of each otherdenote alkyl with 1-4 carbon atoms and cycloalkyl with 3-6 carbon atoms, in which the total number of carbon atoms of R3and R4is more than 3, except for the above case, where one of the radicals R and R4means alkyl with 1-4 carbon atoms, and the other is cyclohexyl.



 

Same patents:

The invention relates to new compounds of the formula (I) with any abscopal HIV replication properties

The invention relates to new biologically active compounds, methods of treating diseases with their use and pharmaceutical compositions based on these compounds

The invention relates to an improved process for the preparation of substituted N-(1,3,5-triazine-2-yl)aminocarbonyl-arylsulfonamides General formula

< / BR>
where R1= Cl, COOCH3;

R2= OCH3N(CH3)2;

R3= CH3, ON=C(CH3)2, ON=C(CH3)C2H5;

R4= H, CH3,

used in agriculture as herbicides and plant growth regulators

The invention relates to a new cyclopropylamino-1,3,5-triazines and their salts of General formula

< / BR>
in which R1- alkyl, cycloalkyl, alkylsilanes; R2bis (2-hydroxyethyl)amino, 3-hydroxy-1-azetidine, 3-methoxy-1-azetidine, 3-oxo-1-azetidine, morpholine-, 4-hydroxypiperidine, thiomorpholine-, S-oxide-thiomorpholine-, S, S-dioxide-thiomorpholine-, 3-thiazolidine, S-oxide-3-thiazolidine, S, S-dioxide-3-thiazolidine or 8-oxa-3-azabicyclo/3,2,1/ Oct-3-yl

The invention relates to new triazine derivatives and herbicides containing the derivatives as an effective ingredient

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

The invention relates to organic chemistry and agriculture, in particular to the derived SIM-triazine as a compound that protects against fetotoksicheskoe actions of herbicides in the cultivation of sunflower (antidote)

The invention relates to organic chemistry and agriculture, in particular derivatives of 1,3,5-triazine as promoters of seed germination

The invention relates to agriculture, and in particular to a method of increasing the number of microorganisms Pseudomonas for wheat

The invention relates to agriculture and chemistry

The invention relates to heterocyclic chemistry and organo-phosphorus compounds, namely melamine salt of bis(oxymethyl)phosphinic acid of formula I (hereinafter referred to as Melafen") and how you can get it

< / BR>
The specified connection is a regulator of growth and development of plants and may find application in agriculture and horticulture

The invention relates to chemistry and agriculture

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention relates to 1,3,5-triazines of general formula I

,

wherein F is C3-C6-cycloalkyl, substituted with C1-haloalkyl or CHR3R4 wherein R3 and R4 are independently C1-C6-alkyl and C3-C6-cycloalkyl, and total amount of carbon atoms in R3 and R4 is 4 or more; R1 is amino, formylamino (C1-C4-alkyl)carbonylamino; R2 isC1-C4-haloalkyl. Also disclosed are intermediates and herbicide composition based on said 1,3,5-triazines.

EFFECT: compounds with high herbicidal activity.

7 cl, 10 tbl, 13 ex

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

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal composition containing synergetically effective amounts of (A) and (B) components, wherein (A) has formula II (R1 is C1-C6-alkyl, substituted with halogen; R2, R3 and R4 are hydrogen; R5 is rest of formula -B1-Y1, wherein B1 is direct bond and Y1 is acyclic C1-C6-hydrocarbon or cyclic C3-C6-hydrocarbon; F is -CH2-CH2-, -CH2-CH2-CH2- and CH2-O-; X are independently halogen or C1-C4-alkoxy; n = 0-2; and (B) represents one or more herbicides, selected from group containing isoprothuron, flufenacet, anylophos, ethoxysulphuron, mecoprop-(P), ioxinyl, florazulam, pendimethalin, MV 100, etc. Also disclosed is method for weed controlling using abovementioned composition.

EFFECT: composition with improved herbicidal action.

12 cl, 23 ex, 23 tbl

Herbicidal agent // 2271659

FIELD: organic chemistry, agriculture, herbicides.

SUBSTANCE: invention relates to herbicidal agent containing compound of general formula I wherein X represents residue X1 or X2 and Z, R1 and R2 are as defined in claim of invention, and additional active substance selected from group containing bromoxynil, dicamba, flufenacete, metolachlor, atrazine, pendimethaline, imazetapir, iodosulfuron, nicosulfuron, 2-amino-4-(1-fluoro-1-methyl)-6-(3-phenyl-1-cyclobuthyl-1-propylamino)-1,3,5-triazine and N-[(4,6-dimethoxy-pyrimidine-2-yl)-aminocarbonyl]-2-dimethylamino-carbonyl-5-formyl-benzenesulfonamide. Compound of formula I and additional active substance are taken in mass ratio of 1:20-10:1, respectively.

EFFECT: agent of high herbicidal activity.

6 cl, 15 ex

Up!