Derivatives of 3-phenylpyrazole, the method of obtaining derivatives of 3 - phenylpyrazole and fungicidal composition

 

(57) Abstract:

Usage: in agriculture. The essence of the invention: derivatives of 3-phenylpyrazole General formula I, where X is H, Hal, NO2, CN, CHO, (C1-C4) AlKS, (C1-C4) AlKOCO; Y and Z independently of each other H, Hal, NO2CN, (C1-C4) AlK, (C1-C4AlKO, possibly substituted atoms, Hal, (C1-C4) AlKSO, naphthyl, benzyloxy, three (C1-C4) AlK - silyl (C1-C4) AlK, both Y and Z cannot be hydrogen, or Y and Z together with the carbon atoms to which they are attached form a 1,3-dioxolane ring, possibly substituted by Hal, R-H, chlorotalonil, benzoyl, (C1-C4) AlKCO, (C1-C4) AlKOCO, possibly substituted NO2or (C1-C4) ALCOA, PhOCO, possibly substituted NO2or (C1-C4) AlKSCO, N (C1-C4) AlKCONH2; the method of obtaining compounds of f-crystals I, where X Is Hal, and R is H, and Z and Y have the values specified by the interaction of compounds f-crystals II with a halogenation agent; fungicidal composition based on compounds of f-crystals I. 3 C. and 5 C. p. F.-ly, 1 Il, 9 PL. The structure of the compounds of formulas I and II

and

The invention relates to new derivatives of 3-phenylpyrazole, to methods for their preparation, to soderzhashcheisya to derive 3-phenylpyrazole General formula

< / BR>
where X is a hydrogen atom or halogen;

the group nitro, cyano, thiocyanato;

the group of alkyl, alkenyl, quinil, alkoxy or alkylthio, and each of these groups can be galogenirovannami;

phenyl or phenoxy, if necessary substituted; amino, substituted or unsubstituted by one or two alkilani or penilai;

group alkylcarboxylic, carbamoyl, carboxyl or benzoyl;

group alkylsulfonyl or alkylsulfonyl,

with the proviso that the alkyl part of all these groups contain 1 to 4 carbon atoms;

Y and Z, equal or different

the atom of hydrogen, but not both, halogen, groupaverage, nitro, nitroso, cyano, thiocyanato, amino, substituted or unsubstituted two alkilani or penilai;

the group of alkyl, alkoxy, or alkylthio, hydroxyalkyl, alkenyl, quinil, alkylsulfonyl, alkylsulfanyl, the alkyl portion of these groups has 1 to 4 carbon atoms and may be galogenirovannami;

phenyl, phenyloxy or phenylthio or benzyl, substituted or unsubstituted in the nucleus;

the group of formyl, acetyl, alkyl - or alkoxy(thio)carbonyl, mono - or di alkylamino-carbonyl or thio, carboxyl, carboxylate, carbamoyl, the alkyl portion of these groups in the th or unsubstituted in the kernel

Y and Z may together form a carbon bridge containing 1 to 4 carbon atoms, of which at least one may be replaced by oxygen atom, sulfur or nitrogen, in addition, the carbon of the bridge may be substituted by at least one halogen atom and/or at least one group of alkyl, alkoxy or alkylthio defined above and can be connected to each double bond with an oxygen atom;

R -

(a) a hydrogen atom, nitro group, amino, hydroxy, cyano, alkyl or haloalkyl, including each 1 to 6 carbon atoms, phenyl which may be substituted by at least one halogen atom, a nitro group or haloalkyl with 1 to 3 carbon atoms;

b) a group S(O)m-R1in which m represents an integer of 0 to 2;

R1-

when m is equal to 0:

group haloalkyl with 1 to 6 carbon atoms,

phenyl or 3-pyridyl, each may be substituted by at least one halogen atom, nitro group, alkyl, haloalkyl, alkoxy, haloalkoxy, the alkyl part of these four groups has 1 to 4 carbon atoms;

when m is 2:

the group of alkyl or alkoxy, each of 1 to 6 carbon atoms and may be substituted by one or more halogen atoms, or a group ALK is XI, each includes 3 to 6 carbon atoms;

the phenyl group which may be substituted by 1 to 5 substituents selected from the group comprising halogen atom, nitro group, alkyl, haloalkyl, alkoxy, haloalkoxy comprising 1 to 4 carbon atoms;

c) the group CH2-NR2R3,

where R2-

alkyl with 1 to 6 carbon atoms, substituted if necessary by the Deputy chosen in the group consisting of cyano, alkoxy, cycloalkyl with 3 to 7 carbon atoms, alkylsulphonyl, alkoxycarbonyl, mono - or dialkylaminoalkyl, alkylsulfanyl, alkylsulfonyl, dialkylaminoalkyl, the alkyl part of which contains 1 to 6 carbon atoms;

alkenyl or quinil with 2 to 6 carbon atoms;

cycloalkyl with 3 to 7 carbon atoms; phenyl or benzyl, and, if necessary, replaced by Deputy chosen in the group comprising halogen atom, cyano group, alkyl, alkoxy, haloalkyl or haloalkoxy with 1 to 9 halogen atoms, alkylsulphonyl, alkoxycarbonyl, the alkyl part of which contains 1 to 6 carbon atoms;

R3represents a group:

Het, Het-alkyl (of 1 to 6 carbon atoms), Het-alkenyl or Het-quinil (each with 3 to 6 carbon atoms), if necessary, replaced by Deputy selected from the group clonil, alkoxycarbonyl, the alkyl portion of which contains from 1 to 6 carbon atoms,

in which Het represents a heterocyclic radical with 5 to 7 atoms of which 1 to 3 heteroatom (nitrogen, oxygen, sulfur), substituted if necessary by the Deputy chosen from the group comprising halogen atom, cyano group, alkyl, alkoxy, haloalkyl or haloalkoxy with 1 to 9 halogen atoms, alkylsulphonyl, alkoxycarbonyl, the alkyl part of which contains 1 to 6 carbon atoms;

dialkylaminoalkyl, the alkyl part of which contains 1 to 6 carbon atoms; cycloalkyl or cycloalkyl (alkyl with 1 to 4 carbon atoms with 3 to 7 carbon atoms; or phenethyl, if necessary, replaced by Deputy chosen from the group comprising halogen atom, cyano group, alkyl or alkoxy, each with 1 to 4 carbon atoms.

In addition, R2and R3can form with the nitrogen atom to which they relate, nitrided cycle with 6 atoms, of which 4 represent carbon atoms, if necessary replaced, and the fifth represents a carbon atom or heteroatom, such as oxygen, sulfur, nitrogen, which may be substituted by an alkyl group with 1 to 6 carbon atoms, himself nitrided cycle may be substituted by one alkylaminocarbonyl, alkylsulfanyl, alkylsulfonyl, alkyl portion of these groups has 1 to 6 carbon atoms, phenylsulfonyl, phenylsulfonyl;

d) the group (CH2)m-R4,

where m is 1 or 2;

R4represents a group of cyano, nitro, alkylsulphonyl, phenylcarbinol, alkoxycarbonyl, mono - or dialkylaminoalkyl, P(O)(alkoxy)2, P(O)(benzyloxy)2, P(O)(phenoxy)2, trialkylsilyl, phenyl, with the proviso that the alkyl radicals of these groups has 1 to 4 carbon atoms and, if necessary, galogenidov, and the phenyl nucleus of the aromatic radicals may be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, a nitro group or an alkyl radical, alkoxy radical, a radical of haloalkyl, radical, haloalkoxy, radical alkoxycarbonyl, the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

e) the group CH(R5)-X-R6,

where R5represents a hydrogen atom or alkyl with 1 to 4 carbon atoms;

X represents an oxygen atom or a group S(O)nin which n is an integer equal to 0 or 2;

R6alkyl with 1 to 4 carbon atoms, substituted if necessary by the Deputy chosen in the group comprising halogen atom, a group of the MOU carbon) and phenyl nucleus may be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, a nitro group or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, (the alkyl part of each of these radicals contains from 1 to 4 carbon atoms);

alkenyl or quinil with 3 to 6 carbon atoms;

phenyl or benzyl can be substituted by 1 to 5 substituents selected in the group comprising halogen atom, a nitro group or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, (1 to 4 carbon atoms),

f) the group CHR7R8,

where R7represents a hydrogen atom, a group of haloalkyl or alkoxy, each of which contains 1 to 4 carbon atoms,

R8represents a halogen atom, hydroxy group, alkoxy, or O-C(O)-R9where

R9a hydrogen atom, alkyl group, haloalkyl, alkenyl with 1 to 4 carbon atoms, tetrahydrofuryl, tetrahydropyranyl or alkoxycarbonyl, the alkyl part of each of these radicals contain 1 to 6 carbon atoms;

g) (X)-R10,

where X represents an oxygen atom or sulfur;

R10the atom of hydrogen or halogen;

the group of alkyl with 1 to 6 carbon atoms, substituted if necessary by the Deputy chosen in the group comprising halogen atom, cyano group, nitro, alkylsulphonyl, alkoxy is Yes; group cycloalkyl with 3 to 6 carbon atoms;

group alkenyl or quinil with 3 to 6 carbon atoms, substituted if necessary by phenyl which may be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, a nitro group or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

the group of phenyl, benzyl 2-pyridyl, 3-pyridyl, 4-pyridyl, and nuclei can be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, nitro group or cyano, or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylcarboxylic or alkoxycarbonyl, the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

the group CH(R11)-X-R12,

where R11represents a hydrogen atom or alkyl with 1 to 4 carbon atoms;

X represents an oxygen atom or a group S(O)p, p is 0 or 2;

R12represents alkyl with 1 to 4 carbon atoms, substituted if necessary by a halogen atom or alkoxy with 1 to 4 carbon atoms, a group alkenyl or quinil with 3 to 6 carbon atoms; a phenyl group or benzyl which may be substituted by 1 to 5 substituents, selected in the group comprising but the PA CH(R11)-NR13R14,

where R13and R14the same or different, are each:

alkyl with 1 to 4 carbon atoms, substituted, if necessary, a cyano group, alkylcarboxylic, alkoxycarbonyl or dialkylaminoalkyl, a halogen atom or alkoxy with 1 to 4 carbon atoms;

the group of phenyl or benzyl can be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, a nitro group, a cyano or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

the group CHR11-R15,

where R11defined above;

R15represents a heterocyclic group NC4R16R17T, in which R16and R17identical or different, represent a hydrogen atom, an alkyl group or alkoxycarbonyl, each with 1 to 3 carbon atoms; T represents an oxygen atom or sulfur, a carbonyl group, or N-R18in which R18represents a hydrogen atom, an alkyl group, formyl, alkylcarboxylic or alkoxycarbonyl, the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

h) group-C(O)-X-R19,

where X represents an oxygen atom, selected in the group comprising halogen atom, the cyano group; the group cycloalkyl with 3 to 6 carbon atoms, substituted if necessary by alkyl with 1 to 3 carbon atoms, trialkylsilyl, phenylsulfonyl, replaced if necessary at least one halogen atom or alkyl group, alkoxycarbonyl, dialkylaminoalkyl; alkyl part of each of these former radicals contain 1 to 4 carbon atoms, a group of cycloalkyl with 3 to 6 carbon atoms, substituted if necessary by alkyl with 1 to 3 carbon atoms;

group alkenyl or quinil with 2 to 6 carbon atoms, substituted if necessary by phenyl which may be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, a nitro group or an alkyl radical;

the group of phenyl, benzyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, and nuclei can be substituted by 1 to 5 substituents selected from the group comprising halogen atom, nitro group or cyano, or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylcarboxylic or alkoxycarbonyl, alkylthio, alkylsulfonyl, alkylsulfanyl, and the alkyl part of each of these radicals contain 1 to 4 carbon atoms;

group phenylalkyl or group heterocyclyl what adilam, 4-pyridium, 2-fullam, 3-fullam, 2-tanila, 3-tanila, and nuclei can be substituted by 1 to 5 substituents selected from the group comprising halogen atom, a nitro group, or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylcarboxylic or alkoxycarbonyl, alkylthio, alkylsulfonyl, alkylsulfanyl;

i) group C(X)-NR20R21,

where X represents an oxygen atom or sulfur;

R20and R21represent each:

a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, substituted if necessary by the Deputy chosen in the group comprising halogen atom, a cyano group, alkylaryl, alkoxycarbonyl, dialkylaminoalkyl, and the alkyl part of each of these former radicals contain 1 to 4 carbon atoms;

group cycloalkyl with 3 to 6 carbon atoms, substituted if necessary by alkyl with 1 to 3 carbon atoms;

group alkenyl or quinil with 3 to 6 carbon atoms;

the group of phenyl, benzyl, whose nuclei can be substituted by 1 to 5 substituents, selected in the group comprising halogen atom, nitro group or cyano, or a radical of the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylcarboxylic or alkoxycarbonyl, alkylthio, alkylsulfonyl, alkylosis to form, in addition, with the nitrogen atom to which they are linked, a cycle with 6 atoms, 4 of which are carbon atoms, if appropriate substituted, and the fifth atom is a carbon atom or heteroatom, such as oxygen, sulfur;

j) group SiR22R23R24,

where R22, R23and R24the same or different, represent each an alkyl group with 1 to 4 carbon atoms or phenyl or benzyl,

k) P(X)R25R26,

where X represents an oxygen atom or sulfur;

R25and R26the same or different, represent each an alkyl group or alkoxy with 1 to 4 carbon atoms, or a phenyl group, phenoxy, benzyl or benzox showing antifungicide properties.

Mostly in the formula X represents a chlorine atom or bromine.

Other preferred derivatives are those in which in formula I and (I bis Y and Z together form a bridge containing 3 or 4 atom.

Other preferred derivatives are those in which in formula I and (I bis Y and Z form a bridge of methylendioxy, in certain cases halogenated.

Preferred derivatives are those in which in formula I and (I bis Y and/or Z Primula bis I and I R is alkyl(1 to 3 carbon atoms)carbonyl, alkyl(1 to 3 carbon atoms)carbonyloxy, phenylcarbinol or phenylcarbamoyloxy.

Derivatives according to the invention can be obtained by various known methods described in "Comprehensive Heterocyclic Chemistry", A. R. Katritzky et C. W. Rees 1984, T. 5, S. 239 241 and 263, Pergamon Press; "Advances in Heterocyclic Chemistry", A. N. Kostet, I. I. Grandberg, 1966, T. 6, S. 391 - 396, Academic Press et "The chemistry of heterocyclic compounds", L. C. Behr, R. Fusco et C. H. Jardoe, 1967, J. Wiley sons.

The first method consists in the reaction of 3-phenylpyrazole formula II in which Y and Z have the same meaning as in formula I, with a halogenation agent (see drawing).

As the halogenation agent can be called a chlorination agent, such as chlorine, preferably in aqueous medium, for example water, or organic, such as acetic acid or carbon tetrachloride, or hypochloraemia acid, hydrochloric acid, in the presence of hydrogen peroxide, acetic acid, or chloride Sulfuryl or N-chloroimide as N-chlorosuccinimide in such a chlorinated solvent like dichloromethane or pentachloride phosphorus.

The chlorination can be carried out with chlorine in the environment of an organic solvent, preferably a lower carboxylic acid, at a temperature of 16 - 30oC and preferably is s can also be N-chlorosuccinimide in the environment of an organic solvent, preferably a chlorinated solvent, such as dichloroethane,1,2-dichloroethane, at a temperature of 0 80oC, preferably 20 - 50oC, the reagents used usually in a stoichiometric molar ratio.

As agent of the synthesized can be called bromine, preferably in an aqueous solvent such as water, in an acidic environment, such as nitric or acetic acid, in the presence or in the absence of such bases as sodium acetate, or an organic solvent, for example chloroform or perbromide pyridine.

Bromination can be accomplished, for example, with bromine in the environment organic solvent such as a lower carboxylic acid, at a temperature of 16oC, preferably at room temperature.

As agent for the salt, you can use the iodine in the presence of gipoglikemicescoy acid or in the presence of a base such as an alkali metal hydroxide or a basic salt such as sodium acetate or in the presence of a salt of Nickel (II). You can use iodine salt of silver (I) of pyrazole of the formula I. it is Possible to use N-iodosuccinimide as described above for N-chlorosuccinimide.

The fluorination can be performed on the basis of 4-amino-3-phenylpyrazole formula V, in which V and ulozhenie 4, then, irradiation of this compound.

The second known method of obtaining derivatives of the formula I, where X is bromine, consists in the reaction of 4-formyl-3-phenylpyrazole formula IV with bromine in acetic acid to obtain 4-bromo-3-phenylpyrazole.

The compounds of formula II can be obtained in a known manner by reaction with a hydrazine derivative of the formula III in which X represents a hydrogen atom and W represents a hydroxyl radical or a chlorine atom and Y and Z have the same meanings as in formula I.

You can get also known derivatives of the formula II, based on derivatives of the formula III in which X represents a hydrogen atom and W represents a group of dialkylamino, Y, and Z are defined above, by reaction of hydrazine hydrate is added at a temperature of 10 to 150oC, preferably 60 to 120oC, suitable in the environment of an organic solvent, preferably a lower carboxylic acids or alcohols in the presence of a catalyst, an organic or mineral acid, the molar ratio of 2 reagents usually stoichiometric.

Derivatives of the formula III in which X represents a hydrogen atom and W represents a group of dialkylamino, Y, and Z are defined above, can be obtained in a known manner, the reaction is toomalatai, preferably in the absence of an organic solvent, dialkyl (preferably dimethyl or diethyl) acetal of N,N-dimethylformamide, at a temperature of 20 130oC and preferably 70 130oC.

The following examples are given to illustrate the methods of preparation and fungicidal activity of the derivatives according to the invention. The structure was confirmed by NMR analysis.

Example 1. Dissolve at room temperature and with stirring, 25 g (rate 0.162 mol) of 2-chloroacetophenone in 60 ml of N,N-dimethylformamide-dimethylacetal. Maintain stirring and heated the reaction mixture for 4 h 30 min up to 80oC. Environment concentrated to dryness under reduced pressure. The residue is absorbed in 150 ml of methylene chloride. The resulting organic solution was washed with water, dried on MgSO4then concentrate. The remainder chromatographic on a column of silica (solvent: heptane/ethyl acetate 50/50). Get to 27.0 g (0,129 mol) of 1-(2-chlorophenyl)3-dimethylamino-2-propen-1-she (compound I) (exit 80 ), in the form of honey, whose structure is confirmed by nuclear magnetic resonance.

Example 2. Working as in example 1, but using the appropriate reagents, get derivatives of the formula III, CBE is the solution of 10.5 g (0,050 mol) of 1-(2-chlorophenyl)3-dimethylamino-2-propen-1-it, obtained in example 1 in 60 ml of ethanol. The reaction mixture was stirred for 5 h at room temperature, then left at rest for 12 h, then concentrated to dryness. The residue is recrystallized from a mixture of heptane/ethyl acetate. Get 6,9 g (0,0386 mol) of 3-(2'-course)-1H-pyrazole, which has a melting point 93oC (exit 77) (compound 60).

Example 4. Working as in example 3, but using the appropriate reagents, get derivatives of the formula II, are given in table. 2.

Example 5. Dissolve at room temperature and with stirring, 3.5 g of 3-(2'-course)-1H-pyrazole obtained in example 3 in 20 ml of acetic acid. Then the reaction medium is poured, drop by drop, a solution 3,76 g (0,0235 mol) of bromine in 20 ml of acetic acid. Maintain stirring for 1 h at room temperature, then acetic acid and the excess of bromine is distilled off under reduced pressure. The remainder absorb methylene chloride and the organic solution washed with water and bicarbonate, then water, then dried on MgSO4, then concentrate to dryness. The residue is recrystallized from pentane. Gain of 3.3 g (0,0128 mol) of 3-(2'-course)-4-bromo-1H-pyrazole, which has a melting point of 80

Example 7. Dissolve with stirring, 6.8 g (of 0.038 mol) of 3-(2'-course)-1H-pyrazole obtained as in example 3, 30 ml of acetic acid. Then give 2.9 g (0,0409 mol) of chlorine in the reaction medium. Maintain stirring for 1 h at room temperature, then distilled acetic acid under reduced pressure. The remainder absorb methylene chloride and the organic solution washed with water and bicarbonate, then water, then dried in Na2SO4, then concentrate to dryness. The remainder chromatographic on a column of silica (solvent: heptane/ethyl acetate 60/40). Obtain 3.6 g of 3-(2'-course)-4-chloro-1H-pyrazole (compound 96), honey (exit 44).

Example 8. 2.3 g (0.015 mol) of 3-(3'-were)-1H-pyrazole (obtained as in example 3), dissolved in 45 ml of dichloromethane at room temperature and under stirring. Then add 2.1 g (0,016 mol) N-chlorosuccinimide, then continue stirring for 60 h at room temperature. Then the reaction mixture was concentrated, then chromatographic on a column of silica (solvent: heptane/ethyl acetate 80/20). Get 1.4 P CLASS="ptx2">

Example 9. Working as in example 8 using the appropriate reagents, get derivatives of the formula I, in which X represent a chlorine atom and which are summarized in table. 4.

Example 10. 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-iodine-pyrazole (compound 137).

Type of 1.03 g (0,0046 mol) N-iodosuccinimide in a solution of 1 g (0,0045 mol) of the corresponding 4H-pyrazole in 50 ml of dichloroethane. The reaction mixture was stirred for 12 h at room temperature, then concentrated to dryness. The resulting residue is purified by passing through a column of silicon dioxide with a mixture of heptane/ethyl acetate 7/3 as solvent and obtain a white powder with a melting point of 142oC, with the release of 79.5

Example 11. 3-(2-chlorophenyl)-4-cyano-pyrazole.

Dissolve 10 g (0,0055 mol) of 2-chlorobenzalmalononitrile at room temperature and under stirring in 30 ml of N,N-dimethylacetal-dimethylformamide by the method of operation described in example 1. 7.5 g (to 0.032 mol) of the thus obtained compound (3-(2-chlorophenyl)-2-cyano-1-dimethylamino-prop-1-EN-3-one (yield 96%) was dissolved in 80 ml of acetic acid, then add 2 ml (0.04 mol) of hydrazine hydrate is added according to the method of operation described in example 1. After trituration in heptane obtain 4.1 g of 3-(2-chlorophenyl)-4-cyano-the azole (compound 139).

2,04 g (0.01 mol) of 3-(2-chlorophenyl)-4-cyano-pyrazole obtained in example 11, United with 2.4 ml of 95-aqueous ethanol and 1.1 ml of H2SO4concentrated support under the phlegm within 6 h of the Reaction medium is poured into water, then extracted with CH2Cl2. The organic phase is dried on MgSO4and then concentrate. The resulting residue is purified by passing through a column of silicon dioxide (CH2Cl2/MeOH 98/2) to obtain a pale yellow oil: yield 36 N analysis of nuclear magnetic resonance 42280.

Example 13. 3-(2-chlorophenyl)-4-thiocarbamyl-pyrazole (compound 140).

In a solution of 10 ml of dimethylformamide saturated with gaseous hydrochloric acid, add gradually 1 g (0,005 mol) of 3-(2-chlorophenyl)-4-cyano-pyrazole obtained in example 11, and 0.75 g (0.01 mol) of diacetamide. The reaction medium is brought to 100oC for 2 h, then cooled to room temperature and poured into water. Then the reaction medium is washed with aqueous sodium bicarbonate solution, then extracted by CH2Cl2. After drying of the organic phase on MgSO2and evaporation, the obtained residue is purified by passing through a column with silica (heptane/ethyl acetate 1/1) to benzodioxol-4-yl)-pyrazole (compound 141).

The intermediate 3-oxo-3-(2,2-debtor-benzodioxol-4-yl)-propanenitrile receive according to the method described in Synthesis, 1983, 308 IC.Krauss, TL. Cupps, DS. Wise et LB. Townsend, condensation of the anion tsianuksusnogo acid with the acid chloride (2.2-debtor-1,3-benzodioxol-4-yl)-carboxylic acid. Then dissolve 5 g (0,022 mol) of 3-oxo-3-(2,2-debtor-1,3-benzodioxol-4-yl)-propanenitrile in 10 ml of N,N-dimethylacetal-dimethylformamide and heated to 70oC. 5.7 g (0,022 mol) of the thus obtained compound (2-cyano-3-(2,2-debtor-1,3-benzodioxol-4-yl)-1-dimethylamino-prop-1-EN-3-one) was dissolved in 50 ml of acetic acid, then add 1.5 ml (0,025 mol) of hydrazine hydrate is added. After passing through the column with silica (heptane/ethyl acetate 6/4) get 2,42 g of pale yellow powder, yield 44 melting point 175oC.

Example 15. 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-formylpyrazole (compound 142).

1.1 g (0,0044 mol) of 4-cyano-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole obtained above in example 14, was dissolved in 10 ml of toluene in a nitrogen atmosphere at -65oWith and add to 5,74 ml (0,0057 mol) of diisobutylaluminium aluminum, dissolved in toluene. After 30 min stirring at -70oC reaction medium is brought gradually to room temperature and paramasivam, then with the help of water 10-aqueous solution of hydrochloric acid adjusted to pH 4. After extraction with ethyl acetate the organic phase is dried on MgSO4and evaporated. Thus obtained oil is triturated in a mixture of heptane and simple diisopropyl ether to obtain a yellow powder. Output 50 melting point 115oC.

Example 16. 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-methyl-pyrazole (compound 143).

12 g of 1-(2,2-debtor-1,3-benzodioxol-4-yl)-propanone obtained by condensation of N,N-dimethylpropanamide with the lithium anion of 2,2-debtor-1,3-benzodioxole, then dissolved in 14.6 g (0.11 mol) of N,N-dimethylacetal-dimethylformamide and heated to 70oC according to the method of operation described in example 1. 25 g (0.05 mol) obtained in this way enaminone dissolved in 130 ml of acetic acid, then add 3.3 ml (0,069 mol) of hydrazine hydrate is added. The resulting crude product was then purified by rubbing in pentane. The output 27 of the melting point 93oC.

Example 17. 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-nitropyrazole (compound 144).

To a solution of 3 g (0,013 mol) of pyrazole (Y H), obtained in example 1 described above, in 60 ml of dichloroethane added gradually at 0oC 6 ml of concentrated sulfuric acid, then 1.92 g (0.019 mol) KNO3portaiture and stirred for 40 minutes The reaction medium is precipitated by adding ice, then filtered to obtain a powder beige. Output 50 melting point 135oC.

Example 18. Tetrafluoroborate 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-diezani-pyrazole (compound 145).

3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-nitro-pyrazole obtained above in example 17, restore 4-amino-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole 0.8 g (of 0.003 mol) of 4-amino-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole dissolved in 10 ml of anhydrous tetrahydrofuran, is added at 0oC to a solution of 10 ml of tetrahydrofuran containing 1 ml (0,0081 mol) epirate boron TRIFLUORIDE. to 0.6 ml (0.005 mol) of tributylamine in solution in 5 ml of tetrahydrofuran added then the reaction mixture. Maintain stirring 1 h at 0oC, then diluted reaction medium with pentane and filtered on sintered glass. After drying to produce a powder beige. The output 37 of melting point 210oC.

Example 19. 4-acetyl-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole (compound 146).

8 g (0.04 mol) of 4-acetyl-(2,2-debtor-1,3-benzodioxole), dissolved in 20 ml of simple ether is added to a suspension of 3.2 g (0.08 mol) 60-tion of sodium hydride in 30 ml of a simple ester, soderjaschegosya diluted with 5 ml of a simple ester, then added to 2 ml of absolute ethanol and 20 ml of water to remove the excess NaH. Then bring the pH of the reaction medium up to 6 by addition of an aqueous solution of 1 N. hydrochloric acid. After simple extraction with ether, drying over MgSO4, evaporation and purification by passing through a column with silica (heptane/ethyl acetate 9/1) to obtain 5 g of pale yellow powder of 1-(2,2-debtor-1,3-benzodioxol-4-yl)-1,3-butanone. The output 52 of melting point 85oC.

2,04 g (0,0084 mol) of the obtained compound is dissolved then 1.23 ml (0,0092 mol) dimethylacetal-N,N-dimethylformamide by the method of operation described in example 1 and heated to 70oC according to the method of operation described in example 1, then append after isolation of the intermediate enaminone to 0,43 ml (0,0092 mol) of hydrazine hydrate is added according to the method of operation described in example 1. The desired compound is recovered from the reaction medium by chromatography on a column of silica (heptane/ethyl acetate 6/4). The output 23 of the melting point 108oC.

Example 20. 4-methylthio-3-(2-nitro-3-chlorophenyl)-pyrazole (compound 147).

7 g (0.035 mol) of (2-nitro-3-chlorophenyl)-acetophenone dissolved in 50 ml of acetic acid, attached to is 1.81 ml (0,0354 mol) of bromine at room temperature. After had 85

1.5 g (0,0061 mol) of (2-nitro-3-chlorophenyl)-methylthiazolidine get attach at 0oC 1.3 g (0.018 mol) methanolate sodium in solution in 10 ml of methanol to 4.7 g (0,0168 mol) of (2-nitro-3-chlorophenyl) bromoacetophenone obtained above.

1.5 g (0,0061 mol) of (2-nitro-3-chlorophenyl)-dimethylacetophenone dissolved in 1.6 ml (0.012 mol) of dimethylacetal-N,N-dimethylformamide by the method of operation described in example 1 and heated to 70oC, then append after isolation of the intermediate enaminone to 2 ml (0,042 mol) of hydrazine hydrate is added according to the method of operation described in example 1. After purification by passing through a column with silica (heptane/ethyl acetate 75/25) to obtain 600 mg of the desired compound. Exit 36% melting point 169oC.

Example 21. 3-(3-bromophenyl)-4-methylsulphonyl-pyrazole (compound 147).

27.8 g (0.1 mol) 3-bromoacetophenone dissolved in 300 ml of acetonitrile added to 10.2 g (0.1 mol) of methylsulfonate sodium and support when phlegm within 8 hours After cooling and evaporation of the acetonitrile reaction medium is washed with water and extracted using CH2Cl2. The resulting crude residue purified by rubbing in a simple diisopropyl ether and receives a yellow powder (3-bromophenylacetate dissolved in 20 ml (0.14 mol) of dimethylacetal-N,N-dimethylformamide and heated to 70oC, then add, after isolation of the intermediate enaminone, 0.3 ml (0,006 mol) of hydrazine hydrate is added according to the method of operation described in example 1. After cleaning by rubbing in a simple diisopropyl ether to produce a powder beige. The output 44 of melting point 140oC.

Example 22. 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-thiocyanato-pyrazole (compound 148).

In a solution of toluene (80 ml) containing 9,03 g (0.04 mol) of 3-oxo-3-(2,2-debtor-1,3-benzodioxol-4-yl)-propanenitrile obtained in example 6, and 3.8 g (0.02 mol) of paratoluenesulfonyl added to 2.3 ml (0,048 mol) of hydrazine hydrate is added. The reaction mixture is heated to 80oC for 2 h After cooling to room temperature, the reaction medium is diluted with ethyl acetate, washed with water and saturated sodium chloride solution. After drying over MgSO4, evaporation of the organic phase are white powder treated by rubbing in a simple ester: 5-amino-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole. The output 62 melting point 152oC.

To a solution of 1.63 g (0,0168 mol) of potassium thiocyanate in 15 ml of methanol, cooled to -70oC add 0.45 ml (0,0088 mol) of bromine in a solution of methanol (5 ml), previously cooled to -70oC. Then added, maintaining the Ola in solution in 5 ml of methanol, cooled to -70oC. the Stirring is maintained for 1 h 30 min at -70oC, then approximately 30 min at room temperature. The treatment of the reaction mixture is performed by adding ethyl acetate, washing with water and saturated sodium chloride solution. After drying over MgSO4, evaporation of the organic phase receive 5-amino-3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-thiocyanatopropyl. The output 80 melting point 264oC.

In a solution of 1.95 g (0,0065 mol) 5-amino-4-thiocyanato-3-(2,2-debtor-1,3-benzodioxol-4-yl)-pyrazole in 25 ml of tetrahydrofuran at 0oC type of 0.94 ml (0,008 mol) of tributylamine in solution in 5 ml of tetrahydrofuran. The reaction mixture was stirred for 1 h 30 min at room temperature, then diluted with ethyl acetate and washed with water. After drying over MgSO4and the solvent is evaporated, the obtained residue chromatographic on a column of silica and receive 3-(2,2-debtor-1,3-benzodioxol-4-yl)-1-(N-tetrahydrofuranyl)-4-thiocyanato-pyrazole. Exit 20 N oil analysis 44694.

0.33 g (0,00094 mol) obtained above amines dissolved at room temperature in 10 ml of methanol for removing the protective groups and add 0,033 g (0,00018 mol) paratoluenesulfonyl. After 1 h p is the target sodium bicarbonate. Dried on MgSO4and evaporation of the organic phase yields a pale-yellow powder - 3-(2,2-debtor-1,3-benzodioxol-4-yl)-4-thiocyanato-pyrazole. Exit 98 melting point 163oC.

Example 23. 1-methyl-3-(2,3-dichloro-phenyl)-4-chloro-pyrazole (compound 149).

Heated at 150oC for 1 h, 1.5 g of 4-chloro-3-(2,3-dichloro-phenyl)pyrazole and 0.40 g dimethylmethylphosphonate. After returning to room temperature environment absorb aqueous solution, saturated NaHCO3, extracted with twice 50 ml of CH2Cl2. The combined organic phases are dried on Na2SO4concentrate under reduced pressure. The crude solid is purified liquid chromatography on a column of silica (solvent: heptane/ACOF [80/20]).

Example 24. Get as in example 23 4-chloro-3-(5-phenyl(substituted)-1-R-pyrazoles of formula I or I bis, which are presented in the table. 5.

Example 25. 1-benzyl-3-(5)-(2', 2'-debtor-1', 3'-dioxolane)-phenyl-4-chloropyrazole (compound 155).

Add a 1.00 g of 4-chloro-3-(2',2'-debtor-1',3'-dioxolane)-phenylpyrazole and 0.75 g of benzyl bromide in 20 ml of absolute methanol solution of sodium methylate derived from 0.10 g of sodium in pieces and 10 ml of absolute methanol at room and low pressure, absorb 80 ml of a mixture of water/ethyl acetate (1/1). The organic phase is dried on MgSO4concentrate under reduced pressure. The crude solid is purified liquid chromatography on a column of silica (solvent: heptane/ethyl acetate 80/20) (see tab. 6).

Example 26. 1(2'-cyanoethyl)-4-chloro-3-(2',2'-debtor-1,3'- dioxolane)-phenylpyrazole (compound 158).

Dissolved in 20 ml of dioxane and 1.00 g of 4-chloro-3-(2',2'-debtor-1',3'-dioxolane)-phenyl-pyrazole and 0.20 g of Acrylonitrile. Add 0,02 ml of 40 aqueous solution of Triton b In methanol. The reaction medium is stirred for 12 h at room temperature, concentrated to dryness under reduced pressure. The residual solid is triturated with 10 ml of heptane, Recuperat by filtration and dried under reduced pressure, the melting point of 83oC.

Example 27. 1-[(trimethylsilyl)methyl]-4-chloro-3-(2'-nitro -3'-chloro)phenyl-pyrazole (compound 159).

Add to 0.85 g of anhydrous potassium carbonate in a solution of 1.30 g of 4-chloro-3-(2'-nitro-3'-chloro)phenyl-pyrazole and 0.70 g of chloride (trimethylsilyl)bromide in 30 ml of N,N-dimethylformamide. The reaction medium is stirred for 12 h at room temperature, diluted with 100 ml of a mixture of simple ether/H2O (1/1). The ether phase is dried on the column with silica (solvent: heptane/ethyl acetate 50/50).

Example 28. Get as in example 27 compounds are presented in table. 7.

Example 29. 1-(chloriform)-4-chloro-3-(2',2'-debtor-1',3'-dioxolane)-phenyl-pyrazole (compound 172).

Heated under the phlegm of thiophosgene (70oC) within 2 h of 1.00 g of 4-chloro-3-(2', 2'-debtor-1', 3'-dioxolane)phenyl-pyrazole and 0.15 ml of thiophosgene in solution in 50 ml of toluene. Reaction medium was concentrated to dryness under reduced pressure. The residue is purified liquid chromatography on a column of silica (heptane/AcOEt 90/10). The melting point 85oC.

Example 30. 1-(benzoyl)-4-chloro-3-(2',2'-debtor-1',3'-dioxolane)-phenyl-pyrazole (compound 173).

0.55 g benzoyl chloride, diluted in 10 ml of anhydrous tetrahydrofuran, is added, drop by drop, to a solution, cooled to 10oC, 1.0 g of 4-chloro-3-(2', 2'-debtor-1', 3'-dioxolane)-phenyl-pyrazole, 0.08 g DMAR and 0.55 ml of triethylamine in 20 ml of anhydrous tetrahydrofuran. The stirring is continued for 2 h at room temperature. Reaction medium was concentrated to dryness under reduced pressure, absorb in 80 ml of a mixture of H2O/ethyl acetate (1/1). The organic phase is dried on MgSO4and concentrate under reduced pressure. The melting point 85oC.

Example 31. Poluchaut-1',3'-dioxolane)-phenyl-pyrazole (compound 177).

5 ml of methylchloroform diluted in 10 ml of anhydrous tetrahydrofuran, is added, drop by drop, to a solution, cooled to 0oC, 1.0 g of 4-chloro-3-(2', 2'-debtor-1',3'-dioxolane)-phenyl-pyrazole, 0.08 g DMAR and 0.55 mg of triethylamine in 20 ml of anhydrous tetrahydrofuran.

The stirring is continued for 2 h at room temperature. Reaction medium was concentrated to dryness under reduced pressure, absorb in 80 ml of a mixture of H2O/AcOEt (1/1). Organicheskuyu dried on MgSO4and concentrate under reduced pressure. Melting point 75oC.

As stated above, get 1-(benzyloxycarbonyl)-4-chloro-3-(2', 2'-debtor-1', 3'-dioxolane)-phenyl-pyrazole (compound 178), melting point 83oC.

Example 33. 1-(tert.-butyloxycarbonyl)-4-chloro-3-(2',2'-debtor 1'3'-dioxolane)-phenyl-pyrazole (compound 179).

to 1.00 g of anhydrous di(tert. -butyloxycarbonyl), diluted in 10 ml of acetonitrile, added, drop by drop, to a solution of 1.0 g 4-chloro-3-(2', 2'-debtor-1', 3'-dioxolane)-phenyl-pyrazole, 0,045 g DMAR and 0.55 ml of triethylamine in 20 ml of acetonitrile. Stirring is continued for 2 h at room temperature. Reaction medium was concentrated to dryness under reduced pressure. Residual tverdal 80/20). The solid has the consistency of meringue.

Example 34. 1-(phenoxycarbonyl)-4-chloro-3-(2'-nitro-3'-chloro) phenyl-pyrazole (compound 180).

Add small parts of 1.0 ml phenylcarbamate to a solution, cooled to 0oC, 1.3 g of 4-chloro-3-(2'-nitro-3'-chloro) phenyl-pyrazole in 20 ml of pyridine. The stirring is continued for 8 h at room temperature. Reaction medium was concentrated to dryness under reduced pressure and absorb 100 ml of a mixture of H2O-ethyl acetate (1/1). The organic phase is dried on MgSO4and concentrate under reduced pressure. The residual solid is purified by recrystallization from a simple diisopropyl ether. The melting point 123oC.

Example 35. Get as in example 34 compound, predstavlenie in table. 9.

Example 36. 1-(isopropylaminocarbonyl)-4-chloro-3-(2',2'-debtor-1',3'-dioxolane)-phenyl-pyrazole (compound 186).

Add, drop by drop, 0.45 g isopropylmalate to a solution of 1.0 g 4-chloro-3-(2', 2'-debtor-1', 3'-dioxolane)- phenyl-pyrazole and 0.50 g of triethylamine in 20 ml of anhydrous dimethylformamide. Stirring is continued for 2 h at room temperature. Processing identical to the processing of example 32. The melting point 135oC.

The add 0.75 g of chloride Totila small parts in a solution of 1.0 g 4-chloro-3-(2', 2'-debtor-1',3'-dioxolane)-phenyl of pyrazole and 0.5 ml of pyridine in 20 ml of toluene. Stirring is continued for 2 h at 40oC. Processing identical to the processing of example 32. The residual solid is purified liquid chromatography on a column of silica (solvent: heptane-ethyl acetate [80/20]). The melting point 100oC.

Example 38. Experience in vivo by Botrytis cinerea on cut the tomato leaf (sensitive sources, resistant to benzimidazole).

Prepare superfine grinding aqueous suspension of the tested active substances having the following composition: active ingredient 60 mg; surfactant tween 80, oleate derived servicenotification, diluted to 10 in water, 0.3 ml, Supplement to 60 ml with water.

This aqueous suspension is then diluted with water to obtain the desired concentration of the active substance.

Tomatoes, cultivated in a greenhouse (sort Marmande), aged 30 days, should be treated by spraying with an aqueous suspension at various concentrations of the test compounds.

After 24 h the leaves are cut and placed in a Petri dish (diameter 14 cm), the bottom of which is pre-equipped with a wet paper pilpel (3 leaf) suspension of spores Botrytiscinerea, sensitive to benzimidazole or resistant to benzimidazole obtained from 15-day-old cultures, put then in a suspension of the calculation of 150,000 units/cm3.

The control was made in 6 days after infection compared to the untreated control sample.

Under these conditions observed at the dose of 1 g/l good (at least 75) or full protection with the following connections:

Botrytis sensitive to benzimidazole: 9, 13, 17, 19, 21, 22, 23, 24, 25, 71, 73, 74, 88, 95, 99, 100, 104, 105, 107, 108, 113, 114, 116, 120, 122, 123, 124, 128, 133, 135, 147, 166, 172, 173, 175, 176, 177, 179, 180, 181, 182, 183, 184, 185.

Example 39. Experience in vivo by Piricularia oryzae responsible for piricularia rice.

Prepare superfine grinding aqueous suspension of the tested active substances having the following composition: active ingredient 60 mg; surfactant tween 80, oleate derived servicenotification, diluted to 10 water 0.3 ml, Supplement to 60 ml with water.

This aqueous suspension is then diluted with water to obtain the desired concentration of the active substance.

Rice planted in cups in a 50/50 mixture enriched with peat and pozzolan process in the growth stage 10 cm by spraying the above voz 15-day culture, put then in a suspension of the calculation of 100000 units/cm3.

Rice plants were placed for 24 h in incubation (25oC, relative humidity 100), then in the camera for observation under the same conditions for 7 days.

The reading was made in 6 days after infection.

Under these conditions were observed at the dose of 1 g/ good (at least 75) or full protection with the following compounds: 12, 17, 19, 21, 24, 25, 72, 78, 81, 84, 87, 95, 99, 100, 101, 103, 104, 105, 107, 108, 110, 111, 112, 113, 114, 116, 117, 118, 120, 122, 123, 124, 127, 128, 129, 130, 133, 134, 135, 141, 166, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 183, 184, 185.

Example 40. Experience in vivo on Plasmopara Viticola.

Prepare superfine grinding aqueous suspension of the tested active substances having the following composition: active substance 60 mg; surfactant tween 80, oleate derived servicenotification, diluted to 10 water 0.3 ml, Supplement 60 ml of water.

This aqueous suspension is then diluted with water to obtain the desired concentration of the active substance.

Cuttings of grape (Vitis vinifera), varieties of Chardonnay, cultivated in the cups. When these plants reach the age of 2 months (stage 8 10 leaves, height of 10 to 15 cm), they are treated by spraying viewt aqueous solution, does not contain active substances.

After drying for 24 h infect each plant by spraying with an aqueous suspension of spores Plasmopara viticola, obtained from the culture of the age of 17 days, and then suspended from the calculation of 100000 units/cm3.

Then the infected plants subjected to incubation for two days at approximately the 18oC, in an atmosphere saturated with moisture, and then for 5 days at approximately 20 22oC at a relative humidity of 90 to 100

The reading is made in 7 days after infection when compared with the control specimens.

Under these conditions observed at the dose of 1 g/l good (at least 75) or full protection with the following connections: 13, 19, 20, 21, 22, 24, 25, 64, 74, 77, 80, 81, 82, 102, 104, 106, 107, 109, 111, 113, 125, 127, 131, 133, 134, 139, 142, 144, 186.

These results clearly show good fungicidal properties of the derivatives according to the invention against fungal diseases of plants caused by fungi belonging to various families, such as Phycomycetes, Basidiomycetes, Ascomycetes, Adelomycetes or Fungi deuteromycota, especially Botrytis sp. Piricularia oryzae, Altermariale mildiou (mildew of grapes).

In the practical application of the compounds according to the invention are rarely used alone. Most often, these Sesto connection according to the invention as described above, mixed with solid or liquid carriers, which is acceptable in agriculture, and with surface-active substances, is also acceptable in agriculture. It is preferable to use inert conventional carriers and conventional surfactants. These compounds also form part of the invention.

These compositions can also contain any other ingredients, for example protective colloids, sticking agents, thickeners, thixotropic agents, penetration agents, stabilizers, chelating organic high-molecular compounds, etc. are Usually compounds used in the invention can be combined with any solid or liquid additives corresponding to the usual methods of obtaining compositions.

In General, the compositions according to the invention usually contain 0.05 to approximately 95 (by weight) of the compounds according to the invention, one or more solid or liquid carriers and, if necessary, one or more surface-active substances.

The term "media" in this case denotes an organic or mineral, natural or synthetic substance, which combine the connection, in order to facilitate its application on the treated plant. Socks, solid fertilizers etc.,) or liquid (water, alcohols, especially butanol, and so on).

Surface-active agent can be an emulsifier, dispersant or wetting agent of ionic or non-ionic type or a mixture of such surfactants. Can be called, for example, salts of polyacrylic acids, salts of lignosulfonic, salt phenolsulfonic or naphthalenesulfonic, polycondensate ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (especially ALKYLPHENOLS or kilfenora), salts of esters sulfosuccinic acids, derivatives of taurine (especially alliterate), complex phosphate esters of alcohols or polyoxyethylene phenols, esters of fatty acids and polyhydric alcohols, derived from the function of sulfates, sulfonates and phosphates previous connections. The presence of at least a surfactant usually is required when the connection and/or inert carrier does not dissolve in water and when applied agent is water.

Thus, the compositions according to the invention for use in agriculture can contain the proposed active substance in a very wide range, sostavljajushhih CLASS="ptx2">

These compositions according to the invention themselves can be quite different forms, solid or liquid.

As forms of solid compositions can be called powders for dusting (containing compounds, which can achieve 100) and granules, especially those produced by extrusion, by compacting, by impregnation of a granulated carrier, granulation-based powder (the content of compounds in these granules is between 0.5 and 80 for these latter cases).

The compounds of formula I can be used in the form of powders for dusting, you can also use a composition comprising 50 g of active substance and 950 g of talc, it is also possible to use a composition comprising 20 g of active substance, 10 g of finely divided silica and 970 g of talc. These components are mixed and pulverized and put the mixture dusting.

As a form of liquid compositions or intended for the formation of liquid compositions when applied can be called solutions, especially water-soluble concentrates, forming the emulsion concentrates, emulsions, concentrated suspensions, aerosols, wettable powders (or powder for spraying), paste.

Forming the emulsion or soluble concentrates thickets is camping them, 0,001 20 active substances.

In addition to the solvent forming the emulsion concentrates can contain, when necessary, 2 to 20 appropriate additives as stabilizers, surfactants, penetration agents, corrosion inhibitors, dyes or agents clutch as above.

On the basis of these concentrates can be obtained by dilution with water, emulsions of any desired concentration, which are particularly suitable for application to crops.

As an example, here is a composition of several forming emulsion concentrates.

Example CE 1 (g/l).

Active ingredient 400

Alkaline dodecylbenzensulfonate 24

Ethoxylated Nonylphenol with 10 molecules of ethylene oxide 16

Cyclohexanone 200

Aromatic solvent Sufficient for 1 litre

According to another formulation forming the emulsion concentrate is used in the following example.

Example CE-2 (g).

Active substance 250

Epoxydecane vegetable oil 25

A mixture of alkylarylsulfonate and simple polyglycolic ether and fatty alcohol 100

Dimethylformamide 50

Xylene 575

Concentrated suspension, the sediment is kept usually 10 75 active substances, 0.5 to 15 surfactant, 0.1 to 10 thixotropic agent, 0 to 10 appropriate additives like defoamers, corrosion inhibitors, stabilizers, penetration agents, and means of coupling and as carrier, water or an organic liquid in which the active substance malorastvorima or insoluble, certain organic solids or mineral salts may be soluble in the carrier to assist in preventing sedimentation or as antifreeze agents for water.

As an example, here's the next part of concentrated suspensions.

Example SC 1 (g).

Connection 500

Polyethoxysiloxane muistiinpanoista 50

Polyethoxysiloxane alkyl phenol 50

Polycarboxylic sodium 20

Ethylene glycol 50

Organopolysiloxane oil (antifoam) 1

Polysaccharide 1,5

Water 316,5

Wettable powders (or powder for spraying) are usually prepare so that they contain 20 to 95 active substances, and they usually contain, in addition to solid carrier, 0 30 wetting, 3 20 dispersant and, when necessary, 0.1 to 10 one or more stabilizers and/or other additives as penetration agents, means to clutch the key, thoroughly mix the active substance in the respective mixers with the additional substances and crushed by mills or other suitable grinders. Thereby obtain powders for spraying, in which the wetting and suspension best; you can obtain a suspension with water at any desired concentration and these suspensions are very advantageously used particularly for application to the leaves.

Instead of wettable powders can be obtained paste. Terms and conditions access to and use of these pastes such conditions and opportunities, wettable powders or powders for spraying.

As an example, here are various formulations of wettable powders (or powders for spraying).

Example PM 1 (%).

Active substance (compound No. 1) 50

Ethoxylated fatty alcohol (wetting agent) 2,5

The ethoxylated phenylethanol (dispersant) 5

Chalk (inert carrier) 42,5

Example 2 PM (%).

Active substance (compound No. 1) 10

Synthetic alcohol type oxo, branched chain, C13, ethoxylated 8 to 10 ethylene oxides (wetting) 0,75

Neutral calcium lignosulfonate (dispersant) 12

Causesa powder contains the same components, as in the previous example, in the following proportions,

Active substance 75

The wetting 1,50

Disperser 8

Calcium carbonate (inert filler) sufficient amount for 100

Example 4 PM (%).

Active substance (compound No. 1) 90

Ethoxylated fatty alcohol (wetting agent) 4

The ethoxylated phenylethanol (dispersant) 6

Example 5 PM (%).

Active substance (compound No. 1) 50

A mixture of anionic and nonionic surfactants (wetting agent) - 2,5

Sodium lignosulphonate (dispersant) 5

Kaolin clay (inert carrier) 42,5

Aqueous dispersions and emulsions, for example compositions obtained by diluting with water wettable powder or forming an emulsion concentrate according to the invention, included in the total scope of the invention. Emulsions can be of the type water-in-oil or oil-in-water and they can have a thick consistency like "mayonnaise".

Compounds according to the invention can be made in the form of forming a dispersion in water of the granules, is also included in the scope of the invention.

These form the dispersion granules with an apparent density, a component usually approximately between 0.3 and 0.6, have a size fastacting substances in these granules is generally between approximately 1% and 90%, mostly between 25% and 90%

The remainder of the granules is composed mainly of a solid filler and, if necessary, surface-active additives, giving granule properties of the dispersive ability of the pigment in water. These granules can be mainly of two different types, depending on whether soluble or insoluble in water held filler. When the filler is soluble in water, it can be mineral or predominantly organic. Received excellent results with urea. In the case of insoluble filler, the latter is mainly mineral such as kaolin or bentonite. He is accompanied by a predominantly surface-active substances (2 to 20 wt. granules), more than half of which, for example, formed of at least a dispersant, mainly anionic, such as alkaline or alkaline-earth polyarticular or alkali or alkaline earth lignosulfonate, a residue formed by non-ionic or anionic wetting, such as alkaline or alkaline-earth alkylnaphthalenes.

In addition, although not necessary, it is possible to add other additives such as defoamers.

The pellet according to the invention can be obtained by mixing the necessary components is e, extrusion and so on). Usually end up crushing, followed by sieving to a particle size selected in the above range.

Mostly it is produced by extrusion, working as described in the examples below.

Example F-6. Forming a dispersion granules.

In mixer blend of 90 wt. the active substance (compound No. 1) and 10 of urea in the crumbs. The mixture is then milled in a pin mill. Get the powder, which is moistened with about 8 wt. water. Wet powder ekstragiruyut in the extruder with a perforated roller. Get the pellets, which are dried, then crushed and sieved to leave only the granules with a size between 150 and 2000 microns.

Example F-7. Forming a dispersion granules.

In a blender mix the following components,

Active substance (compound No. 1) 75

The wetting agent (alkylnaphthalene sodium) 2

Dispersant (polynaphthalene sodium) 8

Insoluble in water and inert filler (kaolin) 15

This mixture granularit in the fluidized bed in the presence of water, then dried, crushed and sieved to obtain granules with a size of between about 0.15 and 0.80 mm

These granules, Monge to prepare combinations with other active substances, especially fungicides, these latter have the form of wettable powders, or granules or aqueous suspensions.

With regard to compositions adapted for storage and for transportation, they contain mostly 0.5 to 95 wt. the active substance.

1. Derivatives of 3-phenylpyrazole General formula I

< / BR>
where X is a hydrogen atom, halogen, nitro, cyano, formyl, (C1-C4) alkylthio, (C1-C4) alkoxycarbonyl,

Y and Z independently of one another represent hydrogen, halogen, nitro, cyano, (C1-C4) alkyl or (C1-C4) alkoxy, possibly substituted by halogen atoms, (C1-C4) alkylsulfonyl, naphthyl, benzyloxy-, three (C1-C4) alkylsilane (C1WITH4) alkyl, and Y and Z both can denote hydrogen, or Y and Z together with the carbon atoms to which they are attached, form a 1,3-dioxolane ring, possibly substituted by halogen atoms,

R is a hydrogen atom, chlorotalonil, benzoyl, (C1-C4) alkylsulphonyl, (C1-C4) alkoxycarbonyl, possibly substituted with halogen or (C1-C4) alkoxycarbonyl, phenoxycarbonyl, possibly substituted by a nitro-group, (C1-C4) alkylthio the e I represents a chlorine atom or bromine.

3. Derivatives PP. 1 and 2, characterized in that in formula I, Y and/or Z represent a hydrogen atom or chlorine.

4. Derivatives PP. 1 2, wherein Y and Z together with the carbon atoms to which they are attached, form a 1,3-dioxolane ring, possibly substituted by halogen atoms.

5. Derivatives PP. 1 to 4, characterized in that R represents a hydrogen atom, (C1-C3) alkylsulphonyl, (C1-C3) alkoxycarbonyl, benzoyl, phenoxycarbonyl.

6. The method of obtaining derivatives of 3-phenylpyrazole General formula Ia

< / BR>
where X is halogen;

Z and Y have the meanings given in paragraph 1 of the formula

characterized in that the derived 3-phenylpyrazole formula II

< / BR>
in which Z and Y are the specified values,

subjected to interaction with a halogenation agent.

7. The method according to p. 6, characterized in that as the halogenation agent used chlorine, bromine, N chlorosuccinimide or N-jodatime and the interaction of lead in the environment organic solvent.

8. Fungicidal composition containing the active principle, a derivative of pyrazole and acceptable in agriculture additives, characterized in that, as derived

 

Same patents:

The invention relates to the derivatives of benzene, substituted heterocyclic ring represented by the General formula

XZ (1) where R cycloalkyl group having 3-8 carbon atoms;

X halogen atom;

The Z group of the formula

-Nor-Nin which cycloalkyl group may be substituted by an alkyl group having 1-6 carbon atoms, to a process for their preparation and herbicides containing them as active ingredient

The invention relates to the derivatives of arylpyrazole, and to their use in compositions for the destruction of arthropod, nematode, helminth and protozoan pests

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

FIELD: organic chemistry, agriculture, fungicide compositions.

SUBSTANCE: invention relates to compounds of formula I

, wherein R1 and R2 are hydrogen or C1-C4-alkyl; X is C3-C8-cycloalkyl, phenyl or styryl, as well as method for production thereof and fungicide composition containing the same. Compounds of present invention have fungicide activity and are useful in effective controlling of deleterious fungi.

EFFECT: compounds and fungicide composition with improved effectiveness.

3 cl, 2 tbl, 4 ex

FIELD: organic chemistry, insecticides, chemical technology.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole of the general formula (1): wherein A means: (A-1) , (A-2) , (A-3) and (A-4) and wherein X represents C-halogen; R1 represents (C1-C4)-alkyl group or halogen-(C1-C4)-alkyl group; A represents any group among (A-1) - (A-4) wherein R4 represents hydrogen atom or (C1-C4)-alkyl group; n = 0, 1 or 2 under condition that R1 represents halogen-(C1-C4)-alkyl group with exception for perhalogenalkyl group when A represents (A-1) and n = 0, and that n doesn't equal 0 when A represents (A-4). Also, invention describes derivative of pyrazole of the formula (2): wherein A means: (A-1) and Y means: (Y-1) , (Y-2) and (Y-3) wherein X, R2, R3 and R4 have values given above; R5 represents hydrogen atom; A represents (A-1); Y means any group among (Y-1) - (Y-3); Z represents halogen atom that are intermediate compounds used for synthesis of the compound (1). Invention describes methods for preparing compounds of the formula (1) and (2) and insecticide comprising compound of the formula (1) as an active component. Insecticide shows high systemic activity, high safety and reduced harmful effect on environment in vicinity areas of its applying.

EFFECT: improved methods for preparing, valuable insecticide properties of compound.

11 cl, 9 tbl, 19 ex

FIELD: organic chemistry, fungicides, agriculture.

SUBSTANCE: invention describes pyrazolcarboxamide of the formula (I) wherein if X means oxygen atom (O) then R1 represents (C1-C3)-alkoxy-(C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means fluorine (F), chlorine (Cl) or bromine atom (Br), and if X means sulfur atom (S) then R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means halogen atom. Also, invention describes a method for preparing compounds of the formula (I), a composition for control of microorganisms and prevention for their attack and damage of plants, and a method for control of phytopathogen organisms, and compound of the formula (V) wherein X means sulfur atom (S); R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means chlorine, bromide or iodine atom. Invention provides control and prevention in infection of plants with phytopathogenic microorganisms - fungi in agriculture and horticulture.

EFFECT: valuable agricultural properties of compounds.

9 cl, 4 tbl, 12 ex

FIELD: agriculture, in particular method for controlling of specific insect pests.

SUBSTANCE: invention relates to method for controlling of lepidopterous, homopterous, hemipterans, coleopterous, and physopods by contacting of said pests or environment thereof with effective amount of compound of formula I SSS1, N-oxide or agriculturally acceptable salt thereof being effective against abovementioned insects, wherein A and B are independently O or S; R1, R2 represent H, C1-C6-alkyl; R3 represents H, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or C3-C6-cycloalkyl; R4 represents H, C1-C6-alkyl, C2-C6-alkinyl, C1-C6-haloalkyl, CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, NO2;. R5 represents H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-hydroxyalkyl, CO2R11R12, halogen or C1-C4-alkoxy; R6 represents H, C1-C6-alkyl, C1-C6-haloalkyl; R7 represents H, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, phenyl ring, benzyl ring, or 5-6-membered heteroaromatic rind, naphthyl ring system, or 8-10-membered condensed heterodicyclic system. Also claimed are compound of formula I and benzoxazine derivative of formula 10 .

EFFECT: compounds effective against agriculture spineless depredators.

22 cl, 13 tbl, 1 dwg, 24 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-pyridylalkylaminopyrazole represented by the following formula (1): wherein X represents C-halogen; R1 represents halogenalkyl group comprising from 1 to 4 carbon atoms with exception of perhalogenalkyl group; R2 represents hydrogen atom; R3 represents hydrogen atom; R4 represents hydrogen atom. Also, invention describes an agent used for control of insects comprising this derivative as an active component. Invention describes two methods for preparing compound of the formula 91). Compounds of the formula (1) are useful for control of insects in agriculture and for domestic animals.

EFFECT: improved preparing methods, valuable properties of compound and agent.

7 cl, 7 tbl, 7 ex

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

Herbicidal agent // 2266648

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal agent containing effective amount of active compound mixture including a) 2-(2-methoxycarbonylsulfonyl aminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazole-3-one of general formula I 1 or sodium salt thereof; and b) one compound improving resistance of agriculture plants, namely diethyl-1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-licarboxylate in ratio a/b of 1:0.025-25 pts.

EFFECT: herbicidal agent reducing damage of agriculture plants, in particular cereals.

1 cl, 24 tbl, 2 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing compound of the formula (I) given in the invention claim wherein substituted are indicated in the description. Method involves interaction of ketone of the formula (II) given in the invention claim with succinic acid anhydride and alkoxide base to yield compound of the formula (III):

. The latter is subjected for interaction with compound of the formula (IV) given in the invention claim to obtain compound of the formula (V):

and interaction of compound of the formula (V) with alcohol to yield the corresponding ester of the formula (VI):

, and interaction of ester with N-methylhydroxylamine. Invention provides enhancing yield, reducing cost as compared to the known methods.

EFFECT: improved preparing method.

9 cl, 6 ex

FIELD: organic chemistry, agriculture, fungicide compositions.

SUBSTANCE: invention relates to compounds of formula I

, wherein R1 and R2 are hydrogen or C1-C4-alkyl; X is C3-C8-cycloalkyl, phenyl or styryl, as well as method for production thereof and fungicide composition containing the same. Compounds of present invention have fungicide activity and are useful in effective controlling of deleterious fungi.

EFFECT: compounds and fungicide composition with improved effectiveness.

3 cl, 2 tbl, 4 ex

FIELD: pharmaceutical industry, medicine.

SUBSTANCE: invention relates to 5-membered N-heterocyclic compounds and salts thereof having hypoglycemic and hypolipidemic activity of general formula I , wherein R1 is optionally substituted C1-C8-alkyl, optionally substituted C6-C14-aryl or optionally substituted 5-7-membered heterocyclic group, containing in ring 1-4 heteroatoms selected from oxygen, sulfur and nitrogen; or condensed heterocyclic group obtained by condensation of 5-7-membered monoheterocyclic group with 6-membered ring containing 1-2 nitrogen atoms, benzene ring, or 5-membered ring containing one sulfur atom; { is direct bond or -NR6-, wherein R6 is hydrogen atom or C1-C6-alkyl; m = 0-3, integer; Y is oxygen, -SO-, -SO2- or -NHCO-; A ring is benzene ring, condensed C9-C14-aromatic hydrocarbon ring or 5-6-membered aromatic heterocyclic ring containing 1-3 heteroatoms selected from oxygen and nitrogen, each is optionally substituted with 1-3 substituents selected from C7-C10-aralkyloxy; hydroxyl and C1-C4-alkoxy; n = 1-8, integer; B ring is nitrogen-containing 5-membered heterocycle optionally substituted with C1-C4-alkyl; X1 is bond, oxygen or -O-SO2-; R2 is hydrogen atom, C1-C8-alkyl, C7-C13-aralkyl or C6-C14-aryl or 5-6-membered heterocyclic group containing in ring 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, optionally substituted with 1-3 substituents; W is bond, C1-C20-alkylene or C1-C20-alkenylene; R3 is -OR8 (R8 is hydrogen or C1-C4-alkyl) or -NR9R10 (R9 and R10 are independently hydrogen or C1-C4-alkyl). Compounds of present invention are useful in treatment of diabetes mellitus, hyperlipidemia, reduced glucose tolerance, and controlling of retinoid-associated receptor.

EFFECT: new medicines for treatment of diabetes mellitus, hyperlipidemia, etc.

26 cl, 518 ex, 3 tbl

FIELD: organic chemistry, fungicides, agriculture.

SUBSTANCE: invention describes 1-pyridinyl-2-azolyl-1-(4-fluorophenyl)ethanols of the general formula (I)

wherein X means nitrogen atom (N) or -CH, and their using as fungicides. Proposed compounds possess high fungicide activity and can be used as agricultural, industrial, medicinal and veterinary fungicides.

EFFECT: valuable properties of compounds.

3 cl, 1 tbl, 4 ex

FIELD: organic chemistry, chemical technology, herbicides.

SUBSTANCE: invention describes new substituted derivatives of pyrazole of the general formula (I): wherein n = 0 or 1; group A represents independently hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms or phenyl group having substituting groups optionally; group D represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkoxy-group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms, halogen atom, alkoxycarbonyl group with 1-4 carbon atoms, alkylsulfonyl group with 1-4 carbon atoms or phenyl group; group E represents hydrogen atom, halogen atom or phenyl group; groups R1 and R2 both represent halogen atom; group R3 represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms or benzyl group; groups R4 and R5 are similar or different and each represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-8 carbon atoms that can be substituted with alkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms, cyanomethyl group or phenyl group; or each R4 and R5 group means benzyl group; or each R4 and R5 group represents α- or β-phenethyl group having substituting groups at benzyl ring optionally. Indicated substituting groups represent alkoxy-groups with 1-4 carbon atoms wherein indicated substituting groups substitute hydrogen atom at the arbitrary positions 0-2 of the benzyl ring; or groups R4 and R5 form in common 5-membered or 6-membered aliphatic ring wherein the indicated ring can be substituted with alkyl groups with 1-4 carbon atoms and indicated ring can comprise one or two heteroatoms chosen from nitrogen oxygen and sulfur atom, and a method for their preparing. Also, invention describes herbicide compositions based on compound of the formula (I). Invention provides preparing herbicide compositions showing the strong herbicide effect and broad herbicide spectrum of their effect.

EFFECT: improved preparing method, valuable properties of derivatives and compositions.

7 cl, 6 tbl, 3 ex

Up!