UA76453C2 - 5-phenylpyrimidines, methods for producing thereof, intermediary compounds, agent and a method for controlling phyto pathogenic fungi - Google Patents

Abstract

The invention relates to 5-phenylpyrimidine of formula (I) wherein the substituents have the following designations: R1 represents a five to ten-membered saturated, partially unsaturated or aromatic monocyclic or bicyclic heterocycle which contains between one and four heteroatoms from the group 0, N or S, and which can be substituted as defined in the description; R2 represents hydrogen, halogen, cyano, alkyl, halogenalkyl or alkoxy; R3 and R4 represent hydrogen, alkyl, halogenalkyl, cycloalkyl, halogencycloalkyl, alkenyl, halogenalkenyl, cycloalkenyl, alkinyl, halogenalkinyl or cycloalkinyl; together with the nitrogen atom to which they are bonded, R3 and R4 can also form a five or six-membered ring which can be split by a heteroatom and can carry at least one substituent; R5 and R6 represent hydrogen, halogen, alkyl, halogenalkyi or alkoxy; R7 and R8 represent hydrogen, halogen, alkyl or halogenalkyl; and R9 represents hydrogen, halogen, alkyl, alkoxy, cycloalkoxy, halogenalkoxy or alkoxycarbonyl. The invention also relates to methods and intermediate products for producing said compounds and the use of the same for controlling pathogenic fungi. (I).

Description

Description of the invention

This invention relates to 5-phenylpyrimidines of formula I,

Kk t -M EE 70 M 9

ЗД В ш--- " with 6 Ж in which the substituents have the following meanings:

B" denotes a five- to ten-membered saturated, partially unsaturated, or aromatic mono- or bicyclic heterocycle containing one to two heteroatoms from the group consisting of O, M, or 5, except pyridyl, and KE may be substituted by one or several identical or different groups of ke,

KU? denotes halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, C.-Cv-alkyl, C.-Ce-haloalkyl, c

C.-C.-alkenyl, C.-C.-alkynyl, C.3-C.e.-cycloalkyl, C.i.-Cv-alkyl, C.-C.-Cv-halogenalkoxy, carboxyl, C.-C.-alkoxycarbonyl, carbamoyl, C.i. -C,-alkyl-aminocarbonyl, C.-Cv-alkyl-C4-Cv-alkylaminecarbonyl, o morpholinocarbonyl, pyrrolidinocarbonyl, C.-C.-alkyl-carbonylamino, C.-Cv-alkylamino, di-(C4-Cv- alkyl)amino,

C.1-Cv-alkylthio, C.-Cv-alkylsulfinyl, C.-Cv-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl,

C.4-Ce-alkylamino-sulfonyl, di-"C4-C-alkyl)aminosulfonyl; co

IN? denotes hydrogen, halogen, cyano, C.4-Cv-alkyl, C.4-Cv-halogenoalkyl, C.-Cv-alkoxy, C.-Cv-haloalkyloxy or C.3-Cv-alkenyloxy;

BZ, 7 denote independently hydrogen, C-C-alkyl, C--Cv-haloalkyl, C3-Ce-cycloalkyl, "

C.-Cv-halocycloalkyl, Co-Cv-alkenyl, Co-Ce-haloalkenyl, C3-C-cycloalkenyl, Co-Ce-alkynyl, co

Co-C6-haloalkynyl or C3-C6-cycloalkynyl;

BZ and 27, together with the nitrogen atom to which they are connected, can form a five- or six-membered ring, which - can be interrupted by a heteroatom from the group that includes O, M or 5 and/or can have one or more substituents from the group which includes halogen, Ci-Cb-alkyl, CgCe-haloalkyl and oxy-Ci-C z-alkylenoxy or in which two adjacent C-atoms or one M-atom and one adjacent C-atom may be C-bonded .-C.-alkylene chain; « 20 VO, V? independently of each other denote hydrogen, halogen, C-C-alkyl, C-C-haloalkyl or -o c C-C-alkoxy; and 27, 28 independently of each other denote hydrogen, halogen, C.1-C6-alkyl or C.-C6-haloalkyl; "» BO denotes hydrogen, halogen, C.-Ci-alkyl, C.i.-Ci-alkyl, C.-Ci-cycloalkyl, C.-Ci-haloalkyloxy,

C.-C -Alkoxycarbonyl or C.-Ce-Alkylaminocarbonyl.

In addition, the invention relates to the method and intermediate products for obtaining these compounds, as well as to their use for combating phytopathogenic fungi. o 2-pyridyl-4-aminopyrimidine derivatives with fungicidal action are known from EP-A 407899, pyridylpyrimidine derivatives are described in OE-A 3937284, OBE-A 3937285, OBE-A 4029649, OBE-A 4034762, OB-A 4227811, EP- A 481405 and MO-A v. 92/10490. page 50 The compounds described in the above publications are suitable as plant protection agents against phytopathogenic fungi. c" Their action in many cases is not satisfactory. Therefore, the task of this invention is to develop compounds with more improved action.

In accordance with this, phenylpyrimidine derivatives of formula I were developed. In addition, a method and intermediate products, as well as means containing them, were developed for combating phytopathogenic fungi and their use for these purposes.

Compounds of the formula | have, in comparison with known compounds, increased effectiveness against phytopathogenic fungi.

Compounds of formula I can be obtained in various ways. 60 Compounds of formula I, in which B" denotes nitrogen-bound heterocycles and B? denotes chlorine, can be obtained, for example, in the following way:

By cyclocondensation of thiourea with complex alkyl ethers of phenyl-malonic acid of the formula IY, compounds of the formula PP, b5 o OB in 5 k-o0 NM are obtained

ХХ Э В -ЖВ--- -о vo МН, в-о 70 6 8 TI ІІІ в в and in the formula ІІ K denotes S-Sev-alkyl. The reaction is usually carried out in a protic solvent, such as alcohols, in particular, ethanol. It can also be carried out in an aprotic solvent, such as pyridine,

M,M-dimethylformamide, M,M-dimethylacetamide or their mixtures (cf. patent OZ 4,331,590; publication Ogo. Rger, 75 apa Rgosey. Ipi, vol. 10, p. 21-27 (1978); SoMesii Slesp. Spet. Sottip., vol. 48, pp. 137-143 (1983);

Neiiiegoai. Spet., Va. 10, pp. 17-23 (1999); Sltesp. Spent Sottip., vol. 58, p. 2215-2221 (1993)).

It may be advantageous to carry out the reaction in the presence of a base that is used in equimolar or excess amounts. Suitable bases are, for example, carbonates and bicarbonates of alkali and alkaline earth metals, for example, potassium and sodium salts, in particular, Ma»hSO»z and ManHsSoO», or nitrogenous bases, such as, for example, pyridine and tributylamine. The reaction temperature is usually from 202C to 2502C, preferably from 702 to 22096.

Usually, the components are used in a close to stoichiometric ratio. It may give advantage to use thiourea in excess amount. The necessary arylmalonic alcohols are known (cf. EP-A 1002788) or can be obtained by methods known from publications. with

Compounds of formula II are converted by alkylating agents of formula II into derivatives of thiobarbituric d) acid. In this formula, K denotes C-C-C-alkyl and X a group that is nucleophilically detached. The formula IM generally refers to conventional alkylating agents such as C and -Cv alkyl halides, in particular methyl chloride and methyl bromide, complex di-(Ci-Cv-alkyl) sulfuric acid esters such as dimethyl sulfate or complex

C.-Cv-alkyl ethers of methanesulfonic acid, such as the complex methyl ether of methanesulfonic acid. o yu o V h

НМ со 9 зв ЖИ Ж вх п---- ша во к

IU 6 8

The reaction can be carried out in water or in a dipolar aprotic solvent, such as, for example, in

M,M-dimethylformamide (cf. patent OB 5,250,689), it mainly occurs in the presence of a base, which can be used in equimolar or excess amounts. As bases, hydroxides are suitable, and? hydrocarbons and carbonates of alkali or alkaline earth metals, such as KOH, Mahon, mMmanso with and

Ma»CoO», as well as nitrogenous bases, such as pyridine. The reaction temperature is usually from 02C to 1002C, preferably from 109 to 6b0eC. Usually, the components are used in a close to stoichiometric ratio. It may be advantageous to use alkylating agents in excess. o Compounds of formula M are converted into dichloropyrimidines of formula MI (cf. OB 4,963,678; EP-A 745593;

OE-A 19642533; UUO-A 99/32458; 9U.Og9u. Spent Va. 58, 5. 3785-3786 (1993); By him Sleep Asia, vol. 64, p. 113-152 (1981)). c 50 and 7 are not theirs

M

IM se KE. 5 Yur at IY 60

As chlorinating agents |SII are suitable, for example, ROSI», RSIU/SiI» or RSI5, or mixtures of these reagents. The reaction can be carried out with an excess amount of chlorinating agent (ROSI 3) or in an inert solvent, for example, acetonitrile or 1,2-dichloroethane. Carrying out the reaction in ROSI»z is preferable.

This interaction is usually carried out at a temperature between 1022 and 180920. From a practical point of view, the reaction temperature usually corresponds to the boiling point of the used chlorinating agent (ROSI) or solvent. The method is preferably carried out with the addition of M,M-dimethylformamide in a catalytic or substoichiometric amount or a nitrogen base, for example, M,M-dimethylaniline.

Amination with a compound of the formula MI! dichloro compounds of the formula MI are converted into compounds of the formula MIP.

Kk

EZ 5 -M In c

M

EI EC: 9 -sh-y -- -- - z k-8- X KE Ui

And --

N UI

And OV

This interaction is usually carried out at a temperature from 02C to 1502C, preferably from 202 to 1202C. publications by U. Spet. Kev. Z (7), pp. 286-287 (1995), Peridz App. Spet., pp. 1703-1705 (1995)| in an inert solvent, if necessary in the presence of an auxiliary base.

Protic solvents such as alcohols, e.g. ethanol, or aprotic solvents such as aromatic hydrocarbons or ethers, e.g. toluene, o-, m- and p-xylene, diethyl ether, diisopropyl ether, tert- butyl methyl ether, dioxane or tetrahydrofuran, in particular, tert-butyl methyl ether or tetrahydrofuran. As auxiliary bases are suitable, for example, MansSoO»z, Ma»SoOz,

Mag HPO,, Ma28507, diethylaniline or ethyldiiso-propylamine.

Usually, the components are used in a close to stoichiometric ratio. However, amine can also be used in excess.

Amines of formula MI are commercially available or known from publications and can be prepared by known methods. with

Thios compounds of the formula MI are oxidized to sulfones IX. at 4 - 7

MV as (oh m their d you

WHOSE dream sl VE... zo E « - (Se)

And 6th -

The reaction is usually carried out at a temperature from 02С to 1002С, preferably from 102С to 502С in the presence of a protic or aprotic solvent | cf. publications: V. Kog. Spent boss, vol. 16, pp. 489-492 (1995); 7. "

Spet., vol. 17, p. 63 (1977)).

Alkyl carboxylic acids such as acetic acid or alcohols such as methanol, water or halogenated hydrocarbons such as dichloromethane or chloroform are suitable solvents. Mixtures of the above solvents can also be used. The best are acetic acid and a mixture of methanol and water. ,» Suitable oxidizing agents are, for example, hydrogen peroxide, pertungstic acid, peracetic acid, 3-chloroperbenzoic acid, perphthalic acid, chlorine, oxygen, and oxoniF (KNZO").

The oxidizing agent is usually used in a stoichiometric ratio. It is also possible to work with an excess amount of oxidizing agent.

Ф Pyrimidine derivatives of formula IIX are converted by interaction with heterocycles of formula X into compounds of formula I. In formula X, cycle A is for a five- to ten-membered saturated, partially unsaturated or their aromatic ring containing nitrogen. from the 50th century

Mkvi ikh vo (jan st.

GF) - in h o ! 60 of them

This interaction reaction is usually carried out at a temperature from 02C to 2002C, preferably from 109 to 1502 in the presence of a dipolar, aprotic solvent, such as M,M-dimethylformamide, tetrahydrofuran or acetonitrile (cf. publication OE-A 3901084; SpPitia, vol. 50 , pp. 525-530 (1996); Kpit. Seiegoivik I. Zoeaip, vol. 12, pp. 1696-1697 (1998)|. 65 Usually, the components are used in a close to stoichiometric ratio. However, it may be preferable to use a nitrogen heterocycle of the formula X in excess

Usually, the reaction is carried out in the presence of a base, which can be in an equimolar or excess amount. As bases suitable hydrocarbonates of alkali and alkaline earth metals, for example, Ma»CO»z and Manso, nitrogen bases, such as triethylamine, tributylamine and pyridine, alcoholates of alkali metals, such as sodium methylate or potassium tert.-butylate, alkali amides metals, such as MaMmN » or hydrides of alkali metals, such as

IN or Man.

Compounds of formula I, in which B is connected through a carbon atom to a pyridine ring, can be obtained, for example, by the following synthesis:

MN, NM in (in) MN (in) : II in 8

HIT

In the formulas UB and ХИ! ring B denotes a carbon-bonded five- to ten-membered, saturated, partially unsaturated or aromatic ring.

The reaction is usually carried out at a temperature from 509C to 2509C, preferably from 1009 to 20090 in the presence of an inert solvent (cf. publications: A!yvigM. U. Spet., vol. 32, p. b669-679 (1979); 9. Og.

Spet., vol. 58, pp. 3785-3786 (1993); Agt. Hit. 2H, vol. 38, M11, p. 718-719 (1985)).

Protic solvents such as alcohols, preferably methanol or ethanol, aprotic solvents such as tributylamine or simple ethylene glycol dimethyl ether are suitable as solvents. at

As a rule, it is preferable to use a base that is taken in an equimolar or excess amount. Suitable bases are alcoholates of alkali and alkaline earth metals, such as sodium methanolate, sodium ethanolate, potassium ethanolate, potassium tert.-butanolate, in particular, sodium methylate, or nitrogenous bases, such as triethylamine, isotriisopropylethylamine and M-methylpiperidine, in particular , pyridine and tributylamine.

Usually, the components are used in a close to stoichiometric ratio. However, it can give IS o) the advantage of using components in excess. at 7 o'clock

SI Kk ich-

M

(C1) to shi s si 6 8 ;"

Chlorination of compound UB into compound MIb is carried out under the same conditions as chlorination of compound M into compound MI.

AND". - And; ;

UM KS VZ

(22).

AND

F! Amination of dichloropyrimidine МИБ to obtain the compound МИ! carried out under the same conditions as the amination of the MI compound into the MIP compound.

Compounds of formula I, where is KE? denotes alkoxy, obtained from the corresponding chlorine compounds of the formula MI (82-SI) by interaction with alcoholates of alkali or alkaline earth metals (cf. publications: Nei(egosusiez, Va. 32, 60 p. 1327-1340 (1991); 9. Neifegosusi. Spet Va. 19, pp. 1565-1567 (1982); Segegoiviki. Boedipus, pp. 400-402 (1991).

Compounds of the formula I, in which K2 denotes cyano, are obtained from the corresponding chlorine compounds of the formula MI (K2-CI) by reaction with cyanides of alkali, alkaline earth metals or such metal cyanides as Masm, b KSM or 7p(SM)". | Wed. publications Neyegosusiev, Va. 39, pp. 345-356 (1994); SoPesi. Blind people Spent Sottype

Va. 60, pp. 1386-1389 (1995); Asia Spit. Zsapa., Va. 50, pp. 58-63 (1996)).

Compounds of formula I, in which VE? denotes hydrogen, obtained from the corresponding chlorine compounds of the formula MI (Е7-СИ) by means of catalytic hydrogenation | cf. publications: U. Rishogipe Speth. Va. 45, pp. 417-430 (1989); 3.

Neyegosusu. Spent Va. 29, pp. 1369-1370 (19923), or by reducing zinc in acetic acid (cf. publications: Ogo. Rger. Rgosead. Ipi., Va. 27, pp. 600-602 (1995); patent UR-A 09 /165379).

Compounds of the formula !, in which B 7 denotes C.i.-Cv-alkyl or C.-Cv-haloalkyl, can be obtained by appropriate transformation of the starting materials of formula II in a similar way to the described synthesis to obtain compounds of the formula !, in which B 2 denotes chlorine. Instead of complex phenylmalonic ether of formula I! complex phenyl-p-ketoether of the formula XII, in which 22 denotes alkyl, is subjected to interaction with thiourea or amidine XII. The following reactions are carried out similarly to compounds with B-chlorine. but oh yush

ME, I'm barely PD. Where do I live at IIT? I; in dk she with V ve and me Z. yuyu

The reaction mixtures are processed by conventional methods, for example, by mixing with water, separating phases, and, if necessary, chromatographic purification of crude products. Intermediate and final products are present in the form of colorless or brownish, viscous oils, which are freed from volatile particles under reduced pressure and, if possible, at elevated temperature. They are purified. If the intermediate and final products are obtained in the form of a solid substance, purification can be carried out by recrystallization or digestion.

If individual compounds of formula I cannot be obtained by the method described above, they can be obtained by derivatization of other compounds of formula |. "

Collective concepts are used for the symbols given in these formulas, which are valid for the following substituents: - c halogen: means fluorine, chlorine, bromine and iodine; c alkyl: means saturated, linear or branched hydrocarbon residues with from 1 to 4, 6 or 8 "" carbon atoms, for example, C1-C6-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, -I 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl

F ii 1-ethyl-2-methylpropyl; g" haloalkyl: denotes linear or branched alkyl groups with from 1 to 8 carbon atoms (given above), and in these groups, hydrogen atoms can be partially or completely replaced by halogen atoms, for example, C.-Co-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,

Fe difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl; alkenyl: refers to unsaturated, linear or branched hydrocarbon residues with 2 to 4, 6 or 8 carbon atoms and a double bond in any position, for example, C"-Cv-alkenyl, such as ethylene, 1-propenyl, o 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, ko 1-methyl-2-propenyl, 2-methyl- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 60 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-33-butenyl, 1,1-dimethyl-2 -propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl , 4-hexenyl,

B-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2- pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 65 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3 -butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2 -butenyl,

1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl- 1-propenyl and 1-ethyl-2-methyl-2-propenyl; alkynyl: means linear or branched hydrocarbon groups with 2 to 4, b or 8 carbon atoms and a triple bond in any position, for example, C o -C 1 -alkynyl, such as ethynyl, 1-propynyl, 2- propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 17-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl- 3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 70 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl , 4-hexynyl, B-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,

3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-i-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3- butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2- ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; cycloalkyl: denotes monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; Alkoxycarbonyl: denotes an alkoxy group with from 17 to b carbon atoms (as given above), which is linked to the skeleton through a carbonyl group (-CO-); oxyalkylenoxy: divalent, linear chain with from 1 to 3 СНо groups, and both valencies

Connected through an oxygen atom to the skeleton, for example: ОСНХО, ОСНХСНХ, and ОСНХСНХ»О; five- to ten-membered, saturated or partially unsaturated heterocycle containing from one to four heteroatoms from the group consisting of oxygen, nitrogen or sulfur: mono- or bicyclic heterocycles (heterocyclyl) containing next to the hydrocarbon members rings from one to three nitrogen atoms and/or an oxygen atom or a sulfur atom, or one or two oxygen and/or sulfur atoms, for example: 2-tetrahydrofuranyl, 3-tetrahydro-furanyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, C -pyrrolidinyl,

C-isoxazolidinyl, d-isoxazolidinyl, B-isoxazolidinyl, C-isothiazolidinyl, 4-isothiazolidinyl, (8) 5B-isothiazolidinyl, C-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl,

B-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, B-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4- oxadiazolidin-5-yl, 1, 2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, c zo 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1, 93,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2- yl, 2,4-dihydrofur-Z-yl, 2,3-dihydrothien-2-yl, that) 2,3-dihydrothien-Z-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien- Z-yl, 2-pyrroline-2-yl, 2-pyrroline-Z-yl, "g

Z-pyrroline-2-yl, Z-pyrroline-Z-yl, 2-isoxazolin-Z-yl, Z-isoxazolin-3-yl, 4-isoxazolin-Z-yl, 2-isoxazolin-4-yl, Z- isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, Z-isoxazolin-5-yl, re) 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, Z- isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, and

Z-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, Z-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, C,4-dihydropyrazol-3-yl, C,4-dihydropyrazol-4-yl,

3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, « 4,5-dihydropyrazol-5-yl , 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, tv) c 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol- 2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,

Z,4-dihydrooxazol-5-yl, Z,4-dihydrooxazol-2-yl, Z,4-dihydrooxazol-Z-yl, Z,4-dihydrooxazol-4-yl, z 2-piperidinyl, Z-piperidinyl, 4 -piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and -I 1,2,4-hexahydrotriazin-3-yl; a five- to ten-membered aromatic heterocycle containing one to four heteroatoms from

Me group that includes oxygen, nitrogen or sulfur: mononuclear or dinuclear heteroaryl, for example: their - B--lene heteroaryl, which contains from one to four nitrogen atoms or from one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups which, along with carbon atoms, may contain from one to four nitrogen atoms or from one to four nitrogen atoms and one sulfur or oxygen atom as 4) ring members, for example, 2-furyl, 3-furyl, 2 -thienyl, Z-thienyl, 2-pyrrolyl, Z-pyrrolyl, Z-isoxazolyl, d-isoxazolyl, B-isoxazolyl, Z-isothiazolyl, d-isothiazolyl, B-isothiazolyl, Z-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl , 2-oxazolyl, 4-oxazolyl, B-oxazolyl, 2-thiazolyl, 4-thiazolyl, B-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4 -oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazole -2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

F) - benzocondensed 5-membered heteroaryl. which contains from one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: 5-membered heteroaryl groups that together with carbon atoms can contain from one to four nitrogen atoms or from one to three nitrogen atoms and one sulfur atom or oxygen as members of a Ring in which two adjacent carbon members or rings, one nitrogen and one adjacent carbon member of the ring may be linked by means of a buta-1,3-diene-1,4-diyl group in which one or two carbon atoms can be replaced by nitrogen atoms; - 5-lene heteroaryl bound through nitrogen. which contains from one to four nitrogen atoms or a nitrogen-bound benzofused 5-ene heteroaryl which contains from one to three nitrogen atoms: 65 5-membered heteroaryl groups which, along with carbon atoms, may contain from one to four nitrogen atoms, respectively, from one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group, in which one or two carbon atoms can be replaced by nitrogen atoms, and these rings are connected to the skeleton through one of the nitrogen members of the ring; - β-membered heteroaryl, which contains from one to three, respectively, from one to four nitrogen atoms: β-membered heteroaryl groups, which along with carbon atoms can contain from one to three, respectively, from one to four nitrogen atoms as ring members, for example: 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3Z -il;

Especially the best forms of execution of intermediate products in terms of substitutes correspond to the residues from B! 70. to B? formula I.

Taking into account the appropriate use for phenylpyrimidines of the formula | the following values of the substitutes are particularly preferable, both individually and in combination with each other:

Compounds of formula I are preferred, in which KE" is an aromatic heterocycle.

In addition, compounds of formula I are preferred, in which B' is a five- or six-membered, in particular, five-membered heterocycle.

Especially preferred are the compounds of formula I, in which B is a heterocycle containing nitrogen.

Along with this, compounds of formula I are preferred, in which B" represents a heterocycle, which is connected to the pyrimidine ring through nitrogen. In the same degree, compounds of formula I are preferred, in which B" represents the following groups: pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, 1,2,3-trizolyl, tetrazolyl, 1,2,3-triazinyl, 1,2,4-triazinyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, furanyl, thiophenyl, thiazolyl, isothiazolyl, and the heterocycle can be connected to the pyrimidine ring through C or M.

Next, the compounds of formula I are preferred, in which ring B" denotes pyridazinyl, pyrimidinyl or pyrazinyl, in particular, 2-pyrimidinyl.

Equally preferable are the compounds of formula I, in which K" denotes optionally substituted by one or i) three groups KU? or va pyrazolyl, pyrrolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, 2-pyridinyl, 2-pyrimidinyl, pyrazinyl or 3-pyridazinyl.

Particularly preferred are compounds of the formula 1, in which B / denotes pyrazolyl, 1,2,3-triazolyl or 1,2,4-triazolyl, in particular, 1-pyrazolyl. oh

Along with this, the compounds of the formula I are preferred, in which the ring K" is replaced by one to three of the same or different following groups: halogen, shydroxyl, cyano, nitro, amino, mercapto, C.i-Cv-alkyl, C.- -Cv-haloalkyl, Co-Cv-alkenyl, Ge

Co-Cv-alkynyl, C3-C8-cycloalkyl, C.-Ci-Alkoxy, C.i-Ce-halogenalkoxy, carboxyl, C.-C.-Alkoxycarbonyl, 32 carbamoyl, C.C.-C,-alkylaminocarbonyl, C. - C-alkyl-C4-Cv-alkylaminocarbonyl, morpholinocarbonyl, - pyrrolidinocarbonyl, C.-Alkylcarbonylamino, C.-Cv-alkylamino, di-(C--Cv-alkyl)amino, C.--Cv-alkylthio,

C1-C8-alkylsulfinyl, C4-C8-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C4-C8-alkylaminosulfonyl or di-(C4-C8-alkyl)aminosulfonyl. "

In particular, the compounds of formula I are preferred, in which the BK cycle is substituted from one to three identical or - 70 different following groups of ВУ with halogen, cyano, nitro, amino, C.C.-Cv-alkyl, C.C.-Cv.-haloalkyl, C .4-C1-Alkoxycarboxyl, C1-C1-Alkoxycarbonyl, carbamoyl, C1-C1-Alkylaminocarbonyl, di-(C4-C1-Alkyl)aminocarbonyl or C1-C1-Alkylcarbonylamino. Especially preferred are compounds of formula I, in which EC is unsubstituted or substituted once by halogen, -1 cyano group, nitro group, methyl or methoxy group.

Compounds of formula I in which K2 does not denote hydrogen are equally preferred.

In addition, the compounds of formula I are preferred, in which K 2 denotes halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkyl, especially halogen.

Compounds of formula I, in which E? stands for chlorine. In addition, the compounds of formula I, in which EZ represents hydrogen, are preferred. c» Equally preferable are the compounds of formula I, in which ВЗ and Е7 independently of each other denote

C.-Cv-alkyl, C.-Cv-haloalkyl, Cz-Ce-cycloalkyl, Co-Cv-alkenyl.

In particular, the compounds of formula I are preferred, in which EZ denotes hydrogen and KE" denotes C-C-haloalkyl.

Next, compounds of formula I are preferred, in which BZ and 27, together with the nitrogen atom to which they are bound, form

HF) a five- or six-membered ring that can be interrupted by an oxygen atom and can have one or two 7 C.4-Cv-alkyl substituents.

Next, the compounds of formula I, in which as VE? and short circuit? do not denote hydrogen. Especially preferred are the compounds of formula I, in which EC? stands for hydrogen.

To the same extent, the compounds of formula I, in which KE? denotes hydrogen and KZ halogen or methyl.

Next, the compounds of formula I are preferred, in which B" and BZ are the same or different and denote hydrogen or halogen.

In addition, compounds of formula I are preferred, in which E? denotes hydrogen, halogen or C.-C.-alkoxy.

Next, the compounds of the formula !, in which B to B" have the values given in formula I, and B 7 represents the following residues: 2-chloro, b-fluorine; 2,6-difluoro; 2,6-dichloro; 2- methyl, 4-fluorine; 2-methyl, β-fluorine; 2-fluorine,

4-methyl; 2,4,6-trifluoro; 2,6-difluoro, 4-methoxy, 2,4-dimethyl and pentafluoro.

EZ ov

M KA yu e-th Their 2

IJ

In addition, compounds of the formula 1, in which B" denotes 2,4,6-trifluoro, are preferred.

In particular, the preferred compounds I are given in the tables below. The groups listed in these tables are particularly preferred substitutes.

Table 1

Compounds of the formula I-1, in which B U denotes fluorine, KE? denotes chlorine and 2", KZ and BE? denote hydrogen, and the combination of residues KZ and 27 corresponds to the compound of one row of table A. sch in B o -AM Е- EE

M so pln lh Vo yu

M - with in (Se)

And 6 of Table 2 "from Compounds of formula 1-1, in which B? and K9 denote fluorine and 2", 28 and KU denote hydrogen, and the combination of "residues BZ and 2" corresponds to the compound of one row of Table A.

Table C

Compounds of formula I-1, in which B? ii 25 denote chlorine and 2", KZ and BU denote hydrogen, and the combination of ВZ residues and ii 27 corresponds to the combination of one row of table A.

Ge") Table 4 1" Compounds of formula 1-1, in which VE? denotes fluorine and BEZ methyl and 2", BZ and 2? denote hydrogen and the combination of BZ and 2? residues corresponds to the compound of one row of Table A. o Table 5 4) Compounds of formula I-1, in which 2, 25th Z denote fluorine and B/ and KZ denote hydrogen, and the combination of BZ and 27 residues corresponds to the combination of one row of table A.

Table 6

Compounds of formula I-1, in which B 5 and K9 denote fluorine, K/ and KZ denote hydrogen and BC? - methoxy and

Gee! the combination of residues KZ and 27 corresponds to the combination of one row of table A.

Table 7 where Compounds of formula 1-1, in which E?, 9, B", K8 and KU denote fluorine and the combination of KZ residues corresponds to the compound of one row of Table A. 6o Table 8

Compounds of formula 1-1, in which B? denotes methyl, KO, BK" and KZ denote hydrogen and K? denotes fluorine and the combination of the residues KZ and 27 corresponds to the compound of one row of table A.

Table 9. Compounds of formula 1-1, in which VE? denotes fluorine, BZ, B" and BZ denote hydrogen and 2? - methyl, and the combination of residues BZ and 27 corresponds to the compound of one row of table A.

Table 10

Compounds of formula 1-1, in which BE and 2? denote methyl and KZ, 2" and 28 denote fluorine and a combination of residues

VZ Her B corresponds to the combination of one row of table A.

Table 11

Compounds of formula I-2, in which B? denotes fluorine, KO denotes chlorine, and B", KZ and BK? denote hydrogen, and the combination of residues ЕЗ and Е7 corresponds to the combination of one row of table A. and Ж in

Zhan t. r Zho at 7: I M zho

Table 12

Compounds of formula 1-2, in which BZ and E5 denote fluorine and B", BZ | U denote hydrogen and a combination of Ha residues

VZ B corresponds to the combination of one row of table A. o

Table 13

Compounds of the formula 1-2, in which B and 25 represent chlorine and B", 28 and E? represent hydrogen and a combination of residues

VZ Her B corresponds to the combination of one row of table A.

Table 14 o

Compounds of formula 1-2, in which VC? denotes fluorine and EZ methyl and VK", BZ and 9 denote hydrogen, and the combination of residues BZ and 2? corresponds to the compound of one row of table A. "

Table 15

Compounds of formula 1-2, in which B?, 25th BEZ denote fluorine and B/ and KZ denote hydrogen and the combination (Ce) of BZ and 2? corresponds to the combination of one row of table A. i-

Table 16

Compounds of formula 1-2, in which B? and 25 denote, B" and 28 - hydrogen and BZ methoxy and the combination of residues BZ and B? corresponds to the compound of one row of table A. "

Table 17

Compounds of formula 1-2, in which 5, 5, 7, ВЕ8 and КЕ? denote fluorine and the combination of BZ residues corresponds to the compound of one row of table A. a Table 18 » Compounds of formula 1-2, in which B? denotes methyl, KZ, B and KZ denote hydrogen and BC? - fluorine and a combination of VZ and 2 residues? corresponds to the combination of one row of table A,

Table 19 and Compounds of formula 1-2 in which B? denotes fluorine, BZ, B" and BZ denote hydrogen and 2? - methyl and the combination

Ge) of the residues VZ and 27 corresponds to the combination of one row of table A. from Table 20

Compounds of the formula 1-2, in which ВЕ and ВЗ denote methyl and КЗ, В" and Е8З denote hydrogen, and the combination of residues 1 ВЗ Her B corresponds to the compound of one row of table A. Table 21

Compounds of the formula I-3, in which B U denotes fluorine, KO denotes chlorine and B/, KZ and B denote hydrogen, and the combination of residues ЕЗ and Е7 corresponds to the compound of one row of table A.

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IZ V is: M in mam M ny

M 9 Mon Fri B 1-3

Table 22

Compounds of formula 1-3 in which 2? and B5 denote fluorine and 2", BZ and 29 denote hydrogen and a combination of residues

VZ Her B corresponds to the combination of one row of table A.

Table 23

Compounds of formula 1-3 in which 2? and B denote chlorine and KE", 28 and 2? - hydrogen, and the combination of BZ and B" residues corresponds to the compound of one row of table A.

Table 24 p

Compounds of formula 1-3, in which B? denotes fluorine and Z? denotes methyl and B", Z and 29 denote hydrogen and o the combination of residues KZ and 27 corresponds to the compound of one row of table A.

Table 25

Compounds of the formula 1-3, in which KU, B5 and VU denote fluorine and B" and BZ denote hydrogen, and the combination of residues KZ and 27 corresponds to the compound of one row of table A. and

Table 26

Compounds of formula 1-3, in which VE? and KU denote fluorine, K/ and KZ denote hydrogen and KE? denotes methoxy and the combination of the residues KZ and 27 corresponds to the compound of one row of the table A.Z

Table 27 (se)

Compounds of formula 1-3, in which BEU, Z, 27, VZ and E? denote fluorine and a combination of BZ residues and corresponds to the m compound of one row of table A.

Table 28

Compounds of formula 1-3, in which B? denotes methyl, KO, BK" and KZ denote hydrogen and K? denotes fluorine and " the combination of residues KZ and 27 corresponds to the compound of one row of table A.

Table 29 - c Compounds of the formula I-3, in which B and B denote fluorine, KO, B and Z denote hydrogen and B? denotes methyl and h» the combination of residues ЕЗ and Е7 corresponds to the compound of one row of table A. " Table 30

Compounds of the formula 1-3, in which ВЕ and ЕЗ denote methyl and КЗ, В" and Е8З denote hydrogen, and the combination of residues ВВЗів- corresponds to the compound of one row of Table A. and Table 31

Ge) Compounds of formula I-4, in which KV? denotes fluorine, B? denotes chlorine and B", KZ and BC? denote hydrogen and the combination of residues ЕЗ and Е7 corresponds to the combination of one row of table A. p 50 syu"

F) name) 60 b5

EE: Eh

ZM B b 9-5 their four SU

Table 32

Compounds of formula 1-4, in which B? and B5 denote fluorine and 2", BZ and 29 denote hydrogen and a combination of residues

VZ Her B corresponds to the combination of one row of table A.

Table 33

Compounds of formula 1-4, in which B? and 25 denote chlorine and VK", C and 29 denote hydrogen and a combination of Ha residues

VZ B corresponds to the combination of one row of table A. o

Table 34

Compounds of formula 1-4, in which B? denotes fluorine and Z? denotes methyl and B", Z and 29 denote hydrogen, and the combination of residues KZ and 27 corresponds to the compound of one row of table A.

Table 35 o

Compounds of formula 1-4, in which KU, 5th E? denote fluorine and В" and ВЗ denotes hydrogen, and the combination of residues КУ цу and ВЕ" corresponds to the compound of one row of table A.

Table 36

Compounds of formula I-4, in which B? and 9 denote fluorine, K'/ and KZ denote hydrogen and KO - methoxy, and the combination of residues KZ and 27 corresponds to the compound of one row of table A.

Table 37

Compounds of formula 1-4, in which BEU, Z, 27, VZ and E? denote fluorine and a combination of VZ residues and corresponds to the compound of one row of table A. "

Table 38

Compounds of the formula 1-4, in which VK 5 denotes methyl, 5, BK" and BEZ denote hydrogen and KO denotes fluorine, and - with the combination of residues ЕЗ and Е7 corresponds to the compound of one row of table A. "from Table 39 " Compounds of formula 1- 4, in which B? denotes fluorine, KZ, B" and 8 denote hydrogen, and KZ - methyl and a combination of residues BZ and 2? corresponds to the combination of one line of table A. - 45 Table 40

Compounds of formula 1-4, in which VZ and 2? denote methyl and 25, B" and BEZ denote hydrogen, and the combination (o) of BZ and 27 residues corresponds to the compound of one row of table A.

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B Compounds | suitable as fungicides. They are distinguished by excellent activity against a wide range of phytopathogenic fungi, in particular, from the class of ascomycetes, deuteromycetes, phycomycetes and basidiomycetes. They are partially systematically active and can be used for plant protection as soil and foliar fungicides. b They are of particular importance in the fight against a number of phytopathogenic fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, corn, cereals, bananas, cotton, soybeans, coffee, sugar cane, grapes, fruit and ornamental plants, and on vegetable crops, such as cucumbers, legumes, tomatoes, potatoes and pumpkins, as well as on the seeds of these plants.

They are especially suitable for the fight against the following plant diseases: byu" - AGegpagia species on vegetable and fruit plants, - Voiguiiz sipegea (gray rot) on strawberry, vegetable, decorative crops and on grapevines, - Segsozroga agaspidisoia on ground nuts, - Eguvirpe sispogaseagit and Zrpiaegoinesa Shiidipea on pumpkins, - Eguvirne dgatipiz (powdery mildew) on grain crops,

F) - species of Rhyzagisht and MepisiShit on various plants, o - species of Neitipipozrogisht on grain crops, - species of Musozrpaigeiia on bananas and peanuts, 60 - Rpuyuorptoga ipGeviapz on potatoes and tomatoes, - Riaztoraga myisoia on grape vine, - Rhodozrpaega Ieisoigisna on apple trees, - Rveshdosegsozrogheiia Negroihispoides on wheat and barley, - species of Rzeidoregopozroga on hops and cucumbers, because - species of Ryssipia on cereals, - Rugisciagia ogugae on rice,

- KPi2osiopia species on cotton, rice and turf, - Zeriogia podoguit on wheat, - Opsipsha pesayug on grapevines, - Owiyado species on cereals and sugar cane, as well as - Mepishgia (scab) species on apple and pear trees.

In addition, compounds | suitable for the control of phytopathogenic fungi such as Raesiotus magiogia in the protection of materials (for example, wood, paper, in dispersions for coatings, fibers, respectively, fabrics) and in the protection of stored stocks. 70 Compounds I are used in such a way that fungi or plants to be protected from damage by them, materials or soil are treated with a fungicidally active amount of the active substance. Application can be carried out both before and after fungal damage to materials, plants or seeds.

Fungicides generally contain between 0.1 and 95%, preferably between 0.5% and 95%, of the active substance.

Consumption rates when used for plant protection, depending on the desired effect, are between 0.01 and 2.0 kg of the active substance per hectare.

When processing seed grain, the amount of active substance from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g per kg of seed material is generally required.

When used to protect materials, respectively, stored stocks, the consumption rate is based on the area of application and the desired effect. Usual rates of consumption for the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to kg of active substance per cubic meter of the material to be treated.

Compounds | can be translated into conventional preparative forms, for example, solutions, emulsions, suspensions, fine powders, powders, pastes and granules. The preparation form depends on the purpose of application, it should in any case provide a thin and uniform distribution of the compound according to the invention.

Preparative forms are obtained in a known manner, for example, by diluting the active substance in solvents and/or fillers, optionally with the use of emulsifiers or dispersants, and when used as a water diluent, other organic solvents can also be used as auxiliary agents. Suitable auxiliary agents are mainly: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone ), amines (for example, ethanolamine, c zo dimethylformamide) and water; fillers, such as natural crushed rocks (for example, kaolin, alumina, talc, chalk) and artificial crushed rocks (for example, highly dispersed silicic acid, silicic acid salts); emulsifiers such as nonionic and anionic emulsifiers (for example, polyoxyethylene ether of fatty alcohol, alkylsulfonates and arylsulfonates) and dispersants such as lignin sulfite spent alkalis and methylcellulose. ise)

Alkali, alkaline earth metal salts and ammonium salts of lignin sulfonic acid, naphthalene sulfonic acid, phenol sulfonic acid, dibutyl naphthalene sulfonic acid, alkyl aryl sulfonates, alkyl sulfates, alkyl sulfonates, sulfates of fatty alcohols, fatty acids, as well as their salts of alkali and alkaline earth metals, sulfate salts are used as surfactants. fatty acid glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of "naphthalene, respectively, naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenolic ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, . tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, condensation products, etc. ethylene oxide of fatty alcohols, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, polyglycol ester acetal of fatty lauryl alcohol, sorbitol ester,

Spent lignin sulfite alkalis and methyl cellulose. -I To obtain solutions, emulsions, pastes, or oil dispersions intended for direct spraying, fractions of mineral oils with medium and high boiling points are used, such as kerosene or me) diesel fuel (oil), tar oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons thereof, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, o cyclohexanone, chlorobenzene, isoform, strongly polar solvents, e.g. , dimethylformamide, 4) diethylsulfoxide, M-methylpyrrolidone, water.

Powder preparations, preparations for dusting and dusting can be made by mixing or co-grinding the active substances with a solid filler. 5B Granulate, for example, a shell, impregnated or homogeneous granulate can be obtained by binding the active substance with solid fillers. Solid fillers can be, for example, (F) mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, ataclau, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium, magnesium oxide, crushed plastic, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and plant products such as grain flour, tree bark flour, wood flour and nut shell flour, cellulose powder and other solids fillers

Preparative forms generally contain between 0.01 and 95% by weight, preferably between 0.1 and 3% by weight of the active substance.

The active substances have a purity from 9095 to 10095, preferably from 9595 to 10095 (according to the NMR spectrum).

Examples of preparative forms: 65 I. weight. particles of the compound according to the invention are thoroughly mixed with 95 wt. particles of fine kaolin. In this way, a tool for dusting is obtained, which contains 5% by weight of the active substance.

IP Note particles of the compound according to the invention are thoroughly mixed with 92 wt. particles of powdered silica gel and weights. particles of paraffin oil, which are sprayed onto the surface of this silica gel. In this way, a preparative form of the active substance with good adhesive ability is obtained (content of the active substance 2Zmas.9o).

Sh. tOvag. part of the compound according to the invention is dissolved in a mixture consisting of Z9Owag. particle of xylene, bvag. particles of the addition product from 8 to 1 mol of ethylene oxide to 1 mol of M-monoethanolamide of oleic acid, 2 wt. parts of the calcium salt of dodecylbenzenesulfonic acid and 2 wt. parts of the product of the addition of 4 mol of ethylene oxide to 1 mol of castor oil (content of the active substance Umas. 9b). 70 IM. 20 kg part of the compound according to the invention is dissolved in a mixture consisting of bOovag. of cyclohexanone particles, weight part of isobutanol, 5 kg. particles of the product of the addition of 7 moles of ethylene oxide to a mole of isooctylphenol and 5 wt. particles of the product of the addition of 40 moles of ethylene oxide to 1 mole of castor oil (the content of the active substance is 1bmas.9b5).

M. 8Ovag. part of the compound according to the invention is well mixed with Weight. particles of the sodium salt of diisobutylnaphthalene-o-sulfonic acid, 1Ovag. particles of the sodium salt of lignin sulfonic acid from spent sulfite alkali and 7 wt. particles of powdered silica gel and ground in a hammer mill (active substance content 8Omas.9b).

E. Stir 9Ovag. particles of the compound according to the invention with 1Ovag. particles of M-methyl-o-pyrrolidone and obtain a solution that is suitable for use in the form of small drops (content of the active substance UOmas.9b).

MI. 20 kg part of the compound according to the invention is dissolved in a mixture consisting of 4Owag. of cyclohexanone particles, weight part of isobutanol, 20 wt. particles of the product of the addition of 7 moles of ethylene oxide to a mole of isooctylphenol and 10 wt. particles of the product of the addition of 400 moles of ethylene oxide to one mole of castor oil. By concentration and fine distribution of the solution in 10,000 Ovag. of water particles, an aqueous dispersion is obtained, which contains

O,O2wag.9o active substance. Gee!

M. 20 kg. part of the compound according to the invention is well mixed with Weight. particles of sodium salt o diisobutylnaphthalene-o-sulfonic acid, 17 wt. particles of the sodium salt of lignin sulfonic acid from spent sulfite alkali and bOvag. particles of powdered silica gel and ground in a hammer mill. By thin distribution of the mixture in 2000Owag. parts of water, a solution for spraying is obtained, which contains 0.9 wt.% of the active substance. co

Active substances can be used as such, in their preparative form or in the form of use prepared from them, for example, in the form of solutions that are subject to direct spraying, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, preparations for dusting, preparations for "I dusting, granulates by spraying, fine-drop spraying, dusting, with dusting or watering. The forms that are used depend on the purpose of application, but in all cases, the most thin distribution of the active substances according to the invention should be ensured. -

Aqueous formulations can be prepared from emulsion concentrates, pastes or wettable powders (powders for spraying, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, substances as such or dissolved in oil can be homogenized in water with the help of wetting agents, adhesion activators, dispersants or emulsifiers. Water-dilutable concentrates may also be prepared, consisting of an active substance, a wetting agent, an adhesion promoter, a dispersant or an emulsifier, and possibly a solvent and oil. и The concentration of the active substance in ready-to-use preparations can vary widely. In general, it ranges from 0.0001 to 1095, mostly from 0.01 to 1905.

Active substances can be used with success at particularly low consumption rates, and there is an opportunity to use preparations with more than U5mas.9o of the active substance or even to use the active substance without additives. bu Different types of oils, herbicides, fungicides, other means of pest control, bactericides can be added to the active substances, if necessary, also immediately before use (mixtures in the tank). These agents can be mixed with the compounds according to the invention in a weight ratio of 1:10 to 10:1. sl 50 The compounds according to the invention in the form of application as fungicides can be used together with other active substances, for example, herbicides, insecticides, growth regulators, fungicides or sb" fertilizers. When mixing compounds I, respectively, fungicides that contain them, with other fungicides, in many cases, an increase in the spectrum of fungicidal action is ensured.

The following list of fungicides that can be used together with the compounds according to the invention explains the possibilities of their combination, but does not limit them. Such fungicides include the following: o - sulfur, dithiocarbonates and their derivatives, such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc dimethyldithiocarbamate, manganese-ethylenebisdithiocarbamate, manganesezincethylenediaminebisdithiocarbamate, imo) tetramethylthiuram disulfides, zinc ammonia complex (M,M-ethylene bisdithiocarbamate), zinc ammonia complex -(M,M'-propylenebis-dithiocarbamate), polymer zinc-(M,M'-propylenebisdithiocarbamate), because M,M'-propylenebis(thiocarbomoyl)disulfide; - nitro derivatives, such as dinitro-(1-methylheptyl)-phenylcrotonate, 2-tert.-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-tert.-butyl-4,6-dinitro-phenylisopropyl carbonate, diisopropyl ether of 5-nitroisophthalic acid; - heterocyclic compounds such as 2-heptadecyl-2-imidazoline-acetate, 65 2,4-dichloro-6b-(o-chloroanilino)---triazine, O,O-diethylphthalimidophosphonothioate, 5-amino-1-bis- -idimethylamino)phosphinyl|-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone,

2-thio-1,3-dithiolo|4,5-B|Yquinoxaline, methyl ester of 1-(butylcarbamoyl)-2-benzimidazole carbamic acid, 2-methoxy-carbonylaminobenzimidazole, 2-(furyl-(2))-benzimidazole, 2-(thiazolyl-(4))-benzimidazole,

IM-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, M-trichloromethylthiotetrahydrophthalimide,

M-trichloromethylthiophthalimide, - diamide of M-dichlorofluoromethylthio-M,M'-dimethyl-M-phenylsulphuric acid, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rhodanmethylthiobenzthiazole, 1,4-dichloro-2, 5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-33-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline, respectively /- its copper salt, 2,3-dihydro-5-carboxanilido -6-methyl-1,4-oxathien, 70 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathien-4,4-dioxide, anilide 2-methyl-5,6-dihydro-4H -pyran-3-carboxylic acid, 2-methylfuran-3-carboxylic acid anilide, 2,5-dimethylfuran-3-carboxylic acid anilide, 2,4,5-trimethylfuran-3-carboxylic acid anilide, cyclohexylamide 2,5-dimethylfuran -Z-carboxylic acid, M-cyclohexyl-M-methoxy-2,5-dimethylfuran-3Z-carboxylic acid amide, methylbenzoic acid 2-anilide, 2-iodo-benzoic acid anilide, 75. M-formyl-M-morpholine- 2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)-formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2- trichloroethane, 2,6-dimethyl-M-tridecylm orpholine, respectively, its salts, 2,6-dimethyl-M-cyclododecylmorpholine, respectively, its salts,

IM-III-(p-tert.-butylphenyl)-2-methylpropyl|-cis-2,6-dimethylmorpholine,

I-III-(p-tert-butylphenyl)-2-methylpropyl|piperidine, 1-(2-(-2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl|- 1H-1,2,4-triazole, 1-(2--2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl|-1H-1,2,4- triazole,

M-(n-propyl)-M-(2,4,6-trichlorophenoxyethyl)-M'-imidazolylurea, 1-"4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4- triazol-1-yl)-2-butanone, 1-"4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, sc dv ( 2,3 5)-1-I3-(2-chlorophenyl)-2-(4-fluorophenyl)-oxiran-2-ylmethylI-1H-1,2,4-triazole, o-(2-chlorophenyl)-o, -(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethyl-amino-4-hydroxy-β6-methyl-pyrimidine, o bis-(p-"chlorophenyl)-3-pyridinemethanol, 1,2-bis -(3-ethoxy-carbonyl-2-thioureido)benzene, 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzene, - strobilurins such as methyl-E-methoxyimino-|oa-(o- tolyloxy)-o-tolyl|acetate, so methyl-E-2-2-(6--2-cyanophenoxy)pyrimidin-4-yloxy|phenyl)-3-methoxy-acrylate, methyl-E-methoxyimino-|c- (2-phenoxyphenyl))acetamide, o methyl-E-methoxyimino-(0-(2,5-dimethylphenoxy)-o-tolyl|acetamide, «I - anilinopyrimidines, such as M-(4,6-dimethylpyrimidine-2 -il)aniline, "co

M-(4-methyl-6-(1-propynyl)pyrimidin-2-ylaniline, M-(4-methyl-b-cyclopropyl-pyrimidin-2-yl|aniline), - phenylpyrroles such as 4-(2, 2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile, - - cinnamic acid amides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylic acid morpholide, - as well as various fungicides, such as dodecylguanidine acetate, 3-3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl|glutarimide, hexachlorobenzene, "ri-methyl-N-(2,6-dimethylphenyl)- M-furoyl(2)alanine, methyl ether 40.01 -M-(2,6-dimethylphenyl)-IM-(2'-methoxyacetyl)alanine, ts M-(2,6-dimethyl-phenyl)-M-chloroacetyl- O | -2-aminobutyrolactone, methyl ester of chri-m-(2,6-dimethylphenyl)-M-(phenylacetyl)alanine, -» 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2 ,4-dioxo-1,3-oxazolidine, 3-3,5-dichlorophenyl(-5-methyl-5-methoxymethyl!|-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl )-1-isopropylcarbamoyl-hydantoin, imide -i IM-(3,5-dichlorophenyl)-1,2-dimethyl-cyclopropane-1,2-dicarboxylic acid, b 2-cyano-IM-(ethylaminocarbonyl)-2-methoxy -imino)acetate copper, 1-(2-(2,4-dichlorophenyl)pentyl|-1H-1,2,4-triazole, 2,4-difluoro-(-(1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, и- M-(3-chloro-2,6-dinitro-4-rifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-amino-pyridine, c 50 1-(bis-(4-fluorophenyl) )-methylsilyl)methyl)-1H-1,2,4-triazole.

Examples of synthesis c» The synthesis stages given in the examples presented below are used with appropriate changes in the starting compounds to obtain other compounds of formula I. The compounds obtained in this way with their physical data are presented in the tables below. 22 Example 1: b-chloro-5-(2-chloro-b6-fluorophenyl)-4-isopropylamino-2-(1-pyrazolyl)-pyrimidine SHHI-11

Gee! a) 5-(2-chloro-6-fluorophenyl)-2-methylthio-4,6(1H,5H)-pyrimidinedione 60.0 g (208 mmol) 2-(2-chloro-b6-fluorophenyl)-malonic ethyl ester acid and 19.0 g (249 mmol) of thioureas are heated in 77 g (41 b mmol) of n-tributylamine for 2.5 hours to 1502C. The obtained ethanol is distilled off. 180 ml of an aqueous solution of 24.9 g (623 mmol) Mmaon is added to the cooled reaction solution. 60 After mixing with 50 ml of cyclohexane and stirring for about 30 minutes, the aqueous phase is separated, mixed with 35.4 g (142 mmol) of methyl iodide and stirred for 16 hours at a temperature from 209C to 2590. After acidification with a diluted solution of NH and stirring for 30 minutes, the precipitate is filtered.

After washing and drying, 16.7 g of the title compound are obtained in the form of white crystals with Tpl. 2502 C (the kind that is open). b) 4,6-dichloro-5-(2-chloro-6-fluorophenyl)-2-methylthio-pyrimidine

A solution of 48.8 g (17 mol) of the product of stage a) in 200 ml of phosphorus oxychloride is heated under reflux after adding 3 ml of dimethylformamide for 40 hours. After distilling off the main amount of phosphorus oxychloride and diluting the residue with complex ethyl ether of acetic acid, water is added at a temperature of 15905 to 209C with stirring. After the separation of the phases, the organic phase is washed with water and a diluted solution of ManNnsSoO»z, then dried and the solvent is separated. 37.5 g of the title compound are obtained in the form of oil, which is used without further purification in stage c).

IR (film): in Ism") - 1558, 1477, 1449, 1353, 1252, 900, 816, 783. c) b-chloro-5-(2-chloro-6-fluorophenyl)-4-iso-propylamino- 2-methylthio-pyrimidine 70 A solution of 37.5 g (324 mmol) of the product of stage b) in 150 ml of anhydrous dichloromethane is mixed with 24 g (40 b mmol) of isopropylamine and stirred for 5 hours at a temperature from approximately 202C to 2520. Then the solvent is distilled off. The residue is loaded into a complex acetic acid ethyl ether and washed with diluted NOSI, water and diluted Manso solution", then dried and the solvent is removed. From the residue after chromatography on silica gel (cyclohexane/methyl-tert.butyl ether from 100:1 to 19:1) 3.4 g are obtained the compound given in title 75 in the form of colorless crystals with a melting point of 94-982C, which are used without further purification at the next stage. d) b-chloro-5-(2-chloro-b6-fluorophenyl)-4-isopropylamino-2- methylsulfonyl-pyrimidine

A solution of 13.3 g (38.4 mmol) of the product of stage c) in 240 ml of anhydrous dichloromethane is mixed at 02C to 59C with 17.2 g (76.6 mmol) of 3-chloroperbenzoic acid. Stir for 1 hour at 02C to 59C and 14 hours at a temperature of approximately 202C to 252C. After distilling off the solvent, the residue is loaded into ethyl acetate, then washed with a 10956 solution of MansSoz." After phase separation, the organic phase is dried and the solvent is removed from it. The residue is digested with a mixture of isopropyl ether and hexane. 11.3 g of the title compound are obtained in the form of colorless crystals with Tpl. 14590-14996, d) b-chloro-5-(2-chloro-6-fluorophenyl)-4-isopropylamino-2-(1-pyrazolyl)-pyrimidine ch 29 A solution of 180 mg (2.64 mmol) of pyrazole in 4 ml of anhydrous dimethylformamide under ice cooling (3 is mixed with 10 mg (2.64 mmol) of Ma (with a 6096 suspension in mineral oil). After stirring for 1 hour, 500 mg (1.32 mmol) of the product of stage d is added to the reaction mixture) and the mixture is stirred for 14 hours at a temperature from 202 to 2523. By adding water, the product is precipitated. After filtration, washing with water and drying, 450 mg of the compound given in the title is obtained in the form of colorless crystals with Tpl. on 1 vBes-1872C. yu

Example 2: "(5)-6-chloro-4-(2,2,2-trifluoro-1-methylethyl)amino-5-(2,4,6-trifluoro-phenyl)-2-(1-pyrazolyl) -pyrimidine C(I-2) a) 5-(2,4,6-trifluorophenyl)-2-methylthio-4,6(1H,5H)-pyrimidinedione (Ce)

Similarly to example 1 (stage a), from 200.0 g of complex diethyl ether of 2-(2,4,6-trifluorophenyl)-malonic acid, 62.9 g of thiourea and 117.4 g of methyl iodide, 115 g of white crystals with Tpl. 2759 (such as are capable of declension). b) 4,6-dichloro-5-(2,4,6-trifluorophenyl)-2-methylthio-pyrimidine

According to example 1 (stage b) with 64.8 g of the product of stage a) after chromatography on silica gel with "

With cyclohexane, 43 g of white crystals are obtained from Tpl. 75960. 2 c c). (5)-6-chloro-5-(2,4,6-trifluorophenyl)-4-(2,2,2-trifluoro-2-methylethylamino)-2-methylthiopyrimidine. A solution of 90.0 g (277 mmol) of the product of stage b) and 120.0 g (113 mmol) of 2,2,2-trifluoro-1-methyl-ethylamine and is stirred for five days at 1502. After dilution with methyl tert.butyl ether and washing with 5M hydrochloric acid separate the phases. After drying, the organic phase is freed from the solvent. After Chromatography on silica gel (cyclohexane, then cyclohexane/methyl-tert.butyl ether in the ratio 85:15) -I obtain 90 g of the compound given in the title in the form of colorless crystals with Tpl. 94-96260, g) (5)-6-chloro-5-(2,4,6-trifluorophenyl)-4-(2,2,2-trifluoro-1-methylethylamino)-2-methylsulfonylpyrimidine

Ф Similarly to example 1 (stage d) from 90.0 g (424 mmol) of the product of stage c), 89 g (9295 from theory) t" of white crystals with Tpl are obtained. 15990, sl 50 d) (5)-6-chloro-4-(2,2,2-trifluoro-1-methylethyl)amino-5-(2,4,6-trifluorophenyl)-2-(1-pyrazolyl) -pyrimidine

Similarly to example 1 (stage d), from 17.0 g (39.2 mmol) of the products of stage d) and 4.00 g (58.8 mmol) of pyrazole, 14.9 g (90 90 from theory) of the title compound in the form of colorless crystals with Tpl. 209960 (9790th according to RHCVT analysis).

Example 3: (5)-6-chloro-4-(2,2,2-trifluoro-1-methylethyl)amino-5-(2,4,6-trifluorophenyl)-2-(1-imidazolyl)-pyrimidine ( I-3)1 o Analogously to example 1 (stage d) from 89.8 mg of imidazole and 249.5 mg of sulfone from example 1, stage d), 0.22 g (9196 from theory) of the title compound is obtained in the form of colorless crystals with Tpl. 172-17392C de Example 4: (5)-6-chloro-4-(2,2,2-trifluoro-1-methylethyl)amino-5-(2,4,6-trifluorophenyl)-2-(1,2 ,4-triazol-1-yl)-pyrimidine (I-41 60 Similarly to example 1 (stage d) from 91.1 mg of 1,2,4-riazole and 24.95 g of sulfone from example 1, stage d) obtain 0, 22 g (91 95 from theory) of the compound indicated in the title in the form of colorless crystals with Tpl. 176-1779S

Example 5: b-chloro-5-(2,4,6-trifluorophenyl)-4-((5)-1,2-dimethylpropyl|amino-2-(pyridazin-3-yl)-pyrimidine (I-5) a) pyridazine-3-carboxamidine

A solution of 1.60 g (0.068 mol) of sodium in 30 ml of anhydrous methanol is mixed with a solution of 53.5 g (0.51 mol) of pyridazine-33-carbonitrile in 100 ml of methanol and stirred for 8 hours at 359, then 29 g of chloride is added to the reaction mixture. ammonium and heated under reflux for about 14 hours.

The mixture is filtered while hot and the solid is removed from the cooled mother liquor by filtration, and 53.0 g of the title compound is obtained.

TN-NMR: 5 (mil. part., DMSO-dv) - 9.75 (bz); 9.6 (a); 8.6 (49); 8.1 (t). b) 4,6-dihydroxy-5-(2,4,6-trifluorophenyl)-2-(3-pyridazinyl)-pyrimidine

A mixture of 18.1 g (0.06 mol) of complex diethyl ether of 2-(2,4,6-trifluoro-phenyl)-malonic acid, 12 g (0.06 mol) of tributylamine and 10.0 g (0.06 mol) of amidine from example 5a ) is heated for approximately 6 hours to 1802C, while ethanol is driven off. After cooling to 60 20-70, the reaction mixture is mixed with 6.3 g 70 (0.158 mol) of sodium hydroxide dissolved in 7 Oml of water and stirred for another 30 minutes. After cooling to 20 290-259, the reaction mixture is extracted with methyl tert.-butyl ether and precipitated from the aqueous phase by acidification. 6b,Og of the title compound is obtained by filtration.

TN-NMR: 5 (mil. part., DMSO-dv) - 9.5 (4); 8.2 (4); 8.0 (hell); 7.2 (t). c) 4,6-dichloro-5-(2,4,6-trifluorophenyl)-2-(3-pyridazinyl)-pyrimidine

A suspension of 5.7 g (0.018 mol) of dihydroxypyrimidine from example 56) in 37 g (0.2 mol) of phosphorus oxychloride is heated for 8 hours to 1202C, then concentrated in a vacuum. The residue is loaded into dichloromethane and water, the organic phase is dried and the solvent is removed from it. After chromatography on silica gel (cyclohexane/ethyl acetate), 2.0 g of the title compound is obtained. "H-NMR: 5 (mil. part., SOCIv) - 9.2 (4); 8.7 (9); 7.8 (aa); 6.9 (9. g) b-chloro-5- (2,4,6-trifluorophenyl)-4-((5)-1,2-dimethylpropyl|amino-2-(pyridazin-3-yl)-pyrimidine

A solution of 200 mg (0.568 mmol) of dichloride from example 5 c) in bml of dimethylformamide after mixing in 1000 mg (1.2 mmol) of (5)-3-methyl-2-butylamine is stirred for 72 hours at 502C, then cooled to 20-2596.

By adding water, the reaction product is precipitated. Filtration yields 200 mg (10095 from theory) of the compound indicated in the text of the title. 7H-NMR: 5 (mil. part., SOSI") - 9.3 (4); 8.5 (a); 7.6 (as); 6.9 (0; 4.5 (t); 4.4 (t); 1.8 (t); 1.1 (9); 0.9 (4). o

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As indicated by the connection a pyrimidinyl of the formula y

Determination of lipophilic parameters of IsokK/ooR du (table I) is carried out in accordance with the rules of the OECD (Intern.

Agreements on economic development) by the method of reverse-phase RHVT. (F) For this purpose, a correlation curve of IsYak/ooR Ou is constructed, based on ten reference substances and evaluated using the lipophilic parameters determined by the extraction method of eight comparative substances.

The commercially available reverse phase C 48 is used as a stationary phase. Chromatographic separation is carried out with methanol and a buffer solution as a mobile phase at a pH of 7.4 under conditions of a constant eluent composition.

The retention time of the reference values yf is converted in accordance with the equation Ф into the capacity factor K, and Ko as the retention time of the non-retarded solvent on the reverse phase Si8 is the dead time of the chromatographic system: bb k- Vl f yiv

The linear correlation of the IsdkK value with the value of IsdR' of the reference values published in the annex to the European Union 92/69 rules gives a linear regression correlation curve.

Lipophilic parameters of IsdR'u of analytes are interpolated after calculating the logarithmic capacity factor IsokK

From the correlation curve of reference values.

The evaluation of the described methods of analysis and the applied reference values takes place with the help of eight comparative substances, the distribution of which is determined using the extraction method.

Examples of action against phytopathogenic fungi.

The fungicidal effect of compounds of the general formula | can be shown using the following tests. 70 The active substances were prepared separately or together in the form of a 1095-th emulsion in a mixture of 7Omas.9o cyclohexanone, 2Omas.bo Mekapikyu 1M (IshepvokYU ARb, a wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 1Omas.buo M/enokU EM (a nonionic emulsifier based on ethoxylated castor oil) and diluted with water to the desired concentration.

Application example 1 - Efficacy against AKegpagia zoyapi on tomatoes

The leaves of potted plants of the variety "Big fleshy tomatoes 51. Riegite" are sprayed until the formation of drops with an aqueous suspension of the active substance, prepared from the original solution, which contains 1095 of the active substance, 6390 of cyclohexanone and 2790 of the emulsifier. The next day, the leaves are infected with an aqueous suspension of zoospores of AKegpagia zoiYapi in a 296th solution of biomalt 0.17x10 bspores/ml. After that, the plants are placed in a steam-saturated chamber with a temperature between 202C and 222C. After 5 days, late blight on untreated infected control plants had developed to such an extent that lesions could be determined visually in 90.

In this test processed bParts/million. active substance 1-1, I-4, from I-12 to I-14, from I-19 to 1-23, 1-29,

I-Z31, 1-32, from I-35 to 1-37, 1-40, 1-41, 1-46, 1-47, 1-51, 1-52, I-54 and I-60 plants in general had no lesions or had lesions up to 7965, while untreated plants had lesions in 10090.

Example 2 Action against Rissipia hesopaiia on wheat (wheat rust) Ge

The leaves of Kapleg variety wheat sprouts grown in pots were dusted with rust spores (Rissipia o hesopaia). After that, the pots were placed for 24 hours in a chamber with high air humidity (from 90 to 95905) and with a temperature from 202 to 2292C. During this time, the spores germinated and germ tubes penetrated into the tissue of the leaves. The next day, the infected plants were abundantly sprayed until the formation of drops with an aqueous composition of the active substance, prepared from the original solution, which contains 1095 of the active substance, 6395 so of cyclohexanone and 2795 of the emulsifier. After drying the sprayed layer, the studied plants were cultivated for 7 days in a greenhouse with a temperature between 2090 and 2290 and with air humidity from 65 to 7095. After that, the degree of development of fungi on the leaves was determined.

Processed in this experiment using bZchast./mln. with the active substance I-1 and I-2, plants were affected by a maximum of 7905, while untreated plants had lesions in 90965.

Example of application C - Effectiveness against net spotting of barley -

The leaves of barley seedlings of the "Idgi" variety grown in pots are sprayed abundantly until the formation of drops with an aqueous composition of the active substance, prepared from the original solution, which contains 1095 of the active substance, 6395 of cyclohexanone, and 2795 of the emulsifier, and 24 hours after drying of the sprayed layer, they are inoculated with an aqueous "suspension of Rugeporpnog ( eges, the causative agent of reticular spotting of barley.

Then the studied plants are placed in a greenhouse with a temperature between 2020 and 2490 and a relative humidity of 95 to 10095. After 1 days, the degree of disease development on the general surface of the leaves is determined visually in 95 days. million active substance 1-1, I-4, from I-12 to 1-14, from I-19 to

I-23, 1-29, 1-32, from I-35 to 1-37, I-40, I-41, 1-47, I-B1, I-52, I-54 and I-60 plants are not had lesions or had lesions up to 10595, while untreated plants had lesions in 9095. and Application Example 4: Efficacy against Voiguiis sipegea on pepper leaves

Ф Pepper seedlings of the "Meiziedieg Idea! EISHe" variety, after they have developed well from 4 to 5 leaves, are sprayed abundantly until the formation of drops with an aqueous composition of the active substance, prepared from the original pi solution, which contains 1095 of the active substance, 6395 of cyclohexanone and 595 of the emulsifier . The next day, the treated 20 plants are inoculated with a Voiguiis sipegea spore suspension, which contains 1.7 x 1 Obspore/ml of a 295% aqueous solution of biomalt. After that, the studied plants are placed in a chamber with a temperature from 222 to 2490 and high air humidity. After 5 days, determine the degree of damage to the leaves visually in 9bo.

In this test, 250 parts per million were processed. active substance 1-1, I-3, I-4, from I-7 to I-9, from I-11 to 1-14, from

I18 to 1-23, from I-29 to 1-32, from I-35 to 1-37, 1-40, 1-47, 1-51, 1-52, 1-54, 1-60, 1- 77, 1-78 and 1-80 25 plants were not affected or had lesions only up to 795, while untreated plants were affected at

GF) 9090.

Application example 5: Protective action against powdery mildew of cucumbers caused by Zrpaegoipesa Shiidipea o Leaves grown in pots of seedlings of cucumbers of the variety "Spipezizspe Zspiapde" in the cotyledon stage are sprayed abundantly until the formation of drops with an aqueous composition of the active substance, prepared from the original solution, which contains 60 1096 active substances substance, 639o cyclohexanone and 590 emulsifier. 20 hours after drying of the sprayed layer, the plants are inoculated with an aqueous suspension of powdery mildew spores of cucumbers (Zrpaegoipesa

Ttiidipea). The plants are then cultivated in a greenhouse with a temperature between 202C and 2420 and a relative humidity of 60 to 8096 for 7 days. Determine visually at 9 o the degree of damage to the surface of the seedling leaves.

In this test, processed with bFrequency/million. active substance 1-1, I-4, from I-12 to 1-14, from I-19 to 1-23, 1-29, 1-31, 1-32, I-35, I-36, I -41, I-47, I-52, I-54, and I-60 plants were unaffected, while untreated plants were affected by 10,096.

Claims (10)

The formula of the invention 1. 5-phenylpyrimidines of the formula that in ге , m" schi ME! -- their z shchhvav and i where the substituents have the following meanings: В! means pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1, 2,3-triazole, tetrazole, 1,2,3-triazine, 1,2,4--riazine, oxazole, isoxazole, 1,3,4-oxadiazole, furan, thiophene, thiazole, isothiazole, and the heterocycle can be linked to the pyrimidine ring through C or M, pyridazine, pyrimidine or pyrazine, and B! can be substituted by one or three identical or different KU groups, K? means halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, C. -Sev-alkyl, S.-Sev-haloalkyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl, C-C-Alkoxy, C-C-halogenalkoxy, carboxyl, C.-C.-Alkoxycarbonyl, carbamoyl, C.-C.-Alkylaminocarbonyl, C.4-C-alkyl-C.-C.-Alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C.4-C--alkylcarbonylamino, C.4 -C6-alkylamino, di-(C4-C6-alkyl)amino, ch 29 C.1-C6-alkylthio, C6-C6-alkylsulfinyl, C6-C6-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl,8 (9 C-C-alkylaminosulfonyl or di-(C-C-alkyl)uaminosulfonyl; IN? means halogen, cyano, C 1 -C 1 -alkyl, C 4 -C 1 -haloalkyl, C 1 -C 6 -alkyl, C 1 -C 1 -haloalkyl, or C.-C alkenyloxy; c zo BZ, 7 independently mean hydrogen, C-C-alkyl, C--Cv-haloalkyl, C3-Ce-cycloalkyl, C-C-halocycloalkyl, C-C-alkenyl, C-Ce-halogenalkenyl, C3-C-cycloalkenyl, C-Ce-alkynyl, or C-Ce-halogenalkynyl or C3-C-cycloalkynyl; "And VZ and B? together with the nitrogen atom to which they are connected, can form a five- or six-membered ring, which can be interrupted by a heteroatom from the group that includes O, M or 5 and/or can have one or more and substituents from the group, which includes halogen, C -C 6 -alkyl, C 4 -C 6 -haloalkyl and oxy-C 3 -C 3 -alkylenoxy, or in which /-/ych- two adjacent C atoms or one M atom and one adjacent C atom can be linked by a C 4-C,-alkylene chain; VU, KU independently of each other mean hydrogen, halogen, C.-Cv-alkyl, C.--Cv-haloalkyl or " S. -Sual KOKsy; 50 27, 28 independently of each other mean hydrogen, halogen, C.-Ce-alkyl or C.-Ce-haloalkyl; C c BO means hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 2 -haloalkyloxy, :c" C 1 -C 6 -alkyloxycarbonyl or C 1 -C 2 - alkylaminocarbonyl. 2. The compound of the formula | according to claim 1, which differs in that the substituents have the following meanings: В! means pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole or tetrazole, which are linked through C or -and M, or 2-pyrimidine, pyrazine or 3-pyridazine, and KE ! has up to three substituents KU", Kk means halogen, hydroxy, cyano, nitro, amino, mercapto, C.4-Cv-alkyl, C--Cv-haloalkyl, Co-Cv-alkenyl, pi C.-Ce-alkynyl, C3-C8-cycloalkyl, C8-C8-alkyl, C8-C8-haloalkyl, carboxyl, C8-C8-alkyl, C8-C8-alkyl, C8-C8-alkyl, C8-C8-alkylaminocarbonyl, C8-C8-alkyl -C4-C8-alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, cC.i-C,-alkylcarbonylamino, C.-Cv-alkylamino, di-(C--Cv-alkyl)damino, C.-Cv-alkylthio, c» C. -C 1 -alkylsulfinyl, C 4 -C 1 -alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C 4 -C 1 -alkylaminosulfonyl or di-(C 1 -C 2 -alkyl)aminosulfonyl; B' means halogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkyl -Alkoxy; BZ, Cl independently of each other mean hydrogen, C.--Cv-alkyl, C.--Cv-haloalkyl, C.-C-cycloalkyl, tov kov boo3ov (F) or C.--Cv-alkenyl; co BZ and КЕ? together with the nitrogen atom to which they are connected, can form a five- or six-membered cycle, which can be interrupted by an oxygen atom and may have a C.-Cv-alkyl substituent; in E?, 2? mean independently of each other hydrogen, halogen or C.-Cv-alkyl; 27, C mean independently of each other hydrogen or halogen; IN? means hydrogen, halogen, C1-C8-alkyl or C1-C8-alkyl. 3. The compound of formula I according to claim 1 or 2, which differs in that KE? means chlorine. 4. The compound of formula I according to any of claims 1-3, which differs in that the combinations of KU-KU substituents have the following values: 2-chloro, b-fluorine; 2,6-difluoro; 2,6-dichloro; 2-methyl, 4-fluoro; 2-methyl, b-fluorine; 2-fluoro, 4-methyl; 2,4,6-trifluoro; 2,6-difluoro, 4-methoxy; 2,4-dimethyl and pentafluoro. 5. The method of obtaining 5-phenylpyrimidines of formula I according to claim 1, where BC! connected through nitrogen and B? means chlorine, which is distinguished by the fact that thiourea is cyclized with a complex phenylmalonalkyl ether of the formula YII a Shk E ' -a z o -x and ge EE where K means C.-Ce-alkyl, with the preparation of compounds of the formula YII 5 a is Eii , 19 nm -th with Z-jAe KE NM o not EE is. and which are subjected to interaction with an alkylating agent of the formula IM B-X, where K means C.-Ce-alkyl and X is a nucleophilic substitution group, with the formation of compounds of the formula M a In E" ' s nm (8) k-5 - Z M o so Sho and IS) which, with the help of a chlorination agent, are converted into dichloropyrimidines of the formula MI in , " Si e M - (Se) zv in-8 - / Z - a ve Z " which by interaction with amino compounds of the formula MII Z V shsh c 7 I » and are converted into pyrimidine derivatives of the formula MI EE , ez - tb vn (22) I tov-v-Y ve s 50 si Ee s» te and compounds of the formula MI are oxidized to obtain sulfones of the formula IX EE , и -ki ge Ei o m Po) in-vo, - and: in 60 SI re which by interaction with heterocyclic compounds of the formula X in b5 where cycle A means a 5- or b--heteroaryl, which contains from one to four atoms selected from nitrogen, oxygen or sulfur , which is selected from the group consisting of pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, 1,2,3-triazine, 1,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, furan, thiophene, thiazole, isothiazole, pyridazine, pyrimidine or pyrazine, and A can be replaced by one or three identical or different K? groups, are converted into compounds of formula I. 6. The method of obtaining 5-phenylpyrimidines of the formula | according to claim 1, where B is connected through a carbon, which differs in that the dichloropyrimidine of the formula Ma I-i t , 0 si i M si i: va C in where the substituents have the values given in claim 1, and (c) means 5 - or β-ene heteroaryl, which contains from one to four atoms selected from nitrogen, oxygen or sulfur, which is selected from the group consisting of pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3 -triazole, tetrazole, 1,2,3-triazine, 1,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, furan, thiophene, thiazole, isothiazole, and a heterocycle connected to a pyrimidine ring through C, pyridazine, pyrimidine or pyrazine, and B can be replaced by one or three identical or different K- groups, are subjected to interaction with an amine of the formula MI! according to claim 5. 7. An intermediate product of the MI formula according to claim 5, which differs in that the combinations of substituents from 22-89 cb have the value according to claim 4. 8. An intermediate of the Mia formula according to claim 6, which differs in that the combinations of substituents from B2-K9 and 9) have the value according to claim 4. 9. Means suitable for combating phytopathogenic fungi, which contains a solid or liquid carrier and a compound of the general formula I according to claim 1. 10. The method of combating phytopathogenic fungi, which is characterized by the fact that mushrooms or materials, plants, soil or seed material, which are subject to protection from phytopathogenic fungi, are treated with an effective amount of the compound of the general formula I according to claim 1. "I Official Bulletin "Industrial Property ". Book 1 "Inventions, useful models, topographies of integrated circuits", 2006, M 8, 15.08.2006. State Department of Intellectual Property of the Ministry of Education and Science of Ukraine. - with . and? -I (o) sh» 1 syu ime) 60 b5