UA112306C2 - Pyrimidine derivatives and use thereof as pesticides - Google Patents

Abstract

The invention relates to novel substituted pyrimidine derivatives of formula (I), to a method for producing said compounds, to agents containing said compounds, and the use thereof as biologically active compounds, in particular for controlling harmful micro-organisms in plant and material protection and as plant growth regulators. , (І)

Description

The present invention relates to new substituted pyrimidine derivatives, methods of preparation of these compounds, compositions containing these compounds, and their use as biologically active compounds, especially for the control of harmful microorganisms for the protection of agricultural crops and for the protection of materials and as plant growth regulators.

It is already known that specific pyrimidine derivatives can be used to protect agricultural crops as fungicides and/or growth regulators (cf. EP-A 0 001 399,

ER-A 0 028 755, ER-A 0 316 663, ER-A 0 131 867). As the environmental and economic requirements for modern active compounds, such as fungicides, are constantly increasing, e.g. with respect to spectrum of activity, toxicity, selectivity, application rate, residue formation and favorable manufacturing, and in addition there may be problems, e.g. with stability, therefore, there is a constant need for the development of new fungicidal compositions, which, at least in some areas, have advantages in comparison with known compositions.

The present invention now provides new substituted pyrimidine derivatives of the formula (I) 6 5

Mach, M in which

X represents O, 5, 50, 50", CH: or represents a simple bond,

K represents hydrogen, alkyl, tri(C1-C3-alkyl)silyl, formyl or acetyl,

represents in each case optionally substituted Ca4-C:i2-alkyl, haloalkenyl, represents 1-propynyl (prop-1-yn-1-yl), haloalkynyl, represents substituted cycloalkyl, or represents optionally substituted aryl,

B2 and KZ are the same or different and represent in each case hydrogen, halogen, cyano, nitro, OH, 5H, CH(-MoO-alkyl), C(alkyl)/"-MO-alkyl), C3-SU-cycloalkyl, C-C-alkyl, C1-C4-haloalkyl, C-C4--alkoxy, C-C--haloalkyl, C1-C4-alkylthio, C-C--haloalkylthio, Cg-C--alkenyl, b2-b. -haloalkenyl, C1-C4-alkynyl, C1-C4-haloalkynyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C--haloalkylsulfonyl, formyl, C2-C4-alkylcarbonyl, C2 -Cv- haloalkylcarbonyl, Co-C5-alukoxycarbonyl, Co-C5-haloalkyloxycarbonyl, C3-C5-alkenyloxy, C3-Cv-alkynyloxy, C5-C5-alkylcarbonyloxy, C2-C5-haloalkylcarbonyloxy, trialkylsilyl, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by halogen, C1-

Z is a C-alkyl, C-C-haloalkyl, C-C4-alkoxy or C2-C4-alkylcarbonyl,

U represents 0, 5, 50 or 50",

B" is hydrogen, fluorine, chlorine or C-C haloalkyl,

The groups 5 are the same or different and represent in each case hydrogen, halogen or optionally substituted alkyl, or together represent the group -СНо-СНео- so that, together with the carbon atom to which they are attached, they form a cyclopropyl ring,

B" represents hydrogen, halogen, C1-Cα-alkyl or C-C4-haloalkyl, and their agrochemically active salts.

Salts thus obtained similarly have fungicidal and/or plant growth regulating properties.

The pyrimidine derivatives that can be used according to the invention may optionally be presented as mixtures of various possible isomeric forms, especially stereoisomers, for example, E and 7 isomers, threo and erythro isomers, and optical isomers, but also, if appropriate, tautomers . Both E and 2 isomers are claimed, and also threo and erythro, and also optical isomers, any mixtures of these isomers, and also possible tautomeric forms.

If it is appropriate, the compounds of formula (I) are presented, in particular, in the form of enantiomers:

6 5 E 6 5 E in Dos in Dos in E sya vi E in. in. 7 7

We We

If the substituents EZ and E are different, then the following diastereomers are not necessarily present in different mixtures: 6 5 E 6 5 E vo, Dos vo Dos do vi E sia vi E v. in. 7 7

Moss Moss M 6 5 E 6 5 E wo y Dos wo Dos w dl s dl v- v- 7 7

We We

Formula (I) provides a general definition of pyrimidine derivatives that can be used in accordance with the invention. Preferred definitions of radicals for the formulas above and below in the present invention are presented below. These definitions apply both to the final products of formula (I) and to all intermediates (see also below under "Illustration of Processes and Intermediates").

X preferably represents 0, 5, CH" or represents a simple bond.

X is especially preferably 0, 5 or CH".

X is most preferably 0.

X is also most preferably CH.

E is preferably hydrogen, methyl, trimethylsilyl, formyl or acetyl.

E is especially preferably hydrogen.

B' is preferably in each case an optionally branched C4-Cv-alkyl, C-

C1-haloalkyl, C1-C1-haloalkenyl, 1-propynyl (prop-1-yn-1-yl), C1-C1-haloalkynyl, C1-C4-alkoxy-C1-

C3-alkyl, C1-C--haloalkyl-C1i-C3-alkyl, tri(C1-C3-alkyl)silyl-C1--C3-alkyl, is substituted C3-SU-cycloalkyl or optionally substituted C3-C7 -cycloalkyl-Ci-C3-alkyl, where the substituents in the cycloalkyl component are selected from the group that includes halogen, Ci-C4-alkyl,

C-C4-haloalkyl, C-C-alkoxy, C-C4-haloalkyl, C-C-haloalkylthio, C-C-alkylthio and phenoxy (which, in turn, can be substituted by halogen or C1-C4- alkyl), and also represents phenyl, which is optionally mono- or trisubstituted by halogen or C.1-C4-alkyl.

AB' especially preferably represents in each case optionally branched C4-Cv-alkyl, C-Cv-haloalkyl, C3-C5-haloalkenyl, 1-propynyl (prop-1-yn-1-yl), C3-Cv- haloalkynyl, C1-C3-Alkoxy-Ci-C8-alkyl, C1-C3-halo-Alkoxy-Ci-C8-alkyl, tri(C1i-C8-alkyl)silyl-Ci-C»-alkyl, is a substituted C3-Sve- cycloalkyl or optionally substituted C3-C6-cycloalkyl-Ci-C2-alkyl, where the substituents in the cycloalkyl component are selected from the group that includes halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkyl, C1-C4-Alkoxy, C1-C4-Haloalkylthio, C--C4-Alkylthio and Phenoxy (which, in turn, can be substituted by fluorine, chlorine, bromine or C1-C4-alkyl), and is also phenyl , which can be mono- or disubstituted by halogen.

AB is most preferably tert-butyl, 1-propynyl (prop-1-yn-1-yl), 1,1,2,2-tetrafluoroethoxymethyl, trimethylsilylmethyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1- methoxycyclopropyl, 1-methylthiocyclopropyl, 1-trifluoromethylcyclopropyl, 1-phenoxycyclopropyl, 1-(2-chlorophenoxy)cyclopropyl, 1-(2-fluorophenoxy)cyclopropyl, 1-(4-

fluorophenoxy)cyclopropyl, 1-(2,4-difluorophenoxy)cyclopropyl, (ZE)-4-chloro-2-methylbut-3-en-2-yl, cyclopropylmethyl, 2,4-difluorophenyl.

AB is particularly preferably tert-butyl, 1-propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 2, 4-difluorophenyl.

IN? and BZ are the same or different and preferably each represents hydrogen, halogen, cyano, nitro, CH(I-MO(C:1-Cv-alkyl)), C(C1-Cv-alkyl (MO(C1-Cv-alkyl )), C3-Cv-cycloalkyl, C1-Ca-alkyl, C1-

Са4-haloalkyl, Сі-С--аlkoxy, Сі-С--haloаlkoxy, Сі-С4-alkylthio, Сі--С4--haloalkylthio, Сге-С--alkenyl,

C2-C6-alkynyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C6-alkylcarbonyl, /C2-C6- alkoxycarbonyl, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C2-C5-alkylcarbonyloxy, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by halogen, C1-

C1-alkyl, C1-C4-haloalkyl, C1-C4-alkyl or C1-C4-alkylcarbonyl.

IN? and KZ are the same or different and especially preferably each represents hydrogen, halogen, cyano, nitro, CH(I-MO(C1-Ca-alkyl)), C(C1-Ca-alkyl).(-MO(Si-Ca -alkyl)), C3-C8-cycloalkyl,

Ci-Ci-alkyl, Ci-Ci-Co-haloalkyl, Ci--Ci-Alkoxy, Ci-Ci-haloalkyl, Ci-C2-alkylthio, /Ci-C2-haloalkylthio, Ci-Ci-Alkylsulfinyl, Ci-Ci- alkylsulfonyl, acetyl, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, or is phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with halogen, C1-C6-alkyl, C1-C6-haloalkyl, C--C0-alkoxy, acetyl .

IN? and BZ are the same or different and most preferably each is hydrogen, fluorine, xpro, bromine, iodine, cyano, nitro, CH(-MOMe), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl, ethyl, n-propyl, isopropyl, n-, i-, b- or tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, difluorochloromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, or in each case optionally fluoro-, chloro-; bromo-, iodo-, methyl-, ethyl-, trifluoromethyl-, trichloromethyl-, difluoromethyl-, dichloromethyla, difluorochloromethyl-, methoxy-, acetyl-monosubstituted phenyl, phenoxy or phenylthio.

B2 and EZ are especially preferably hydrogen.

U is mostly O or 5.

U is especially preferably 0.

In is also particularly preferably 5.

B" preferably represents hydrogen, fluorine, chlorine, or C-C-Haloalkyl.

B" especially preferably represents hydrogen, fluorine, chlorine, difluoromethyl, trifluoromethyl or difluorochloromethyl.

B" is most preferably hydrogen, fluorine or chlorine.

B» and 29 are the same or different and preferably each represents hydrogen, fluorine, chlorine, bromine, iodine, C-C4-alkyl or C-C--haloalkyl, or together represent the group -CH»-CHe-.

Vo and 5 are the same or different and especially preferably each represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl, or together represent the group -"СН2-СНе-".

Vo and K9 are the same or different and most preferably each represents hydrogen or methyl, or together represent the group -СН2-СНе-.

B" preferably represents hydrogen, fluorine, chlorine, bromine, Ci-Ca-alkyl or Ci-Co-haloalkyl.

B" especially preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, trifluoromethyl or difluorochloromethyl.

B' is most preferably hydrogen, chlorine, methyl, difluoromethyl, trifluoromethyl or difluorochloromethyl.

A further embodiment of this invention relates to compounds of formula (I) in which EC, Ki

VZ each simultaneously represent hydrogen.

A further embodiment of this invention relates to compounds of formula (I), in which E, EC? and

BZ each simultaneously represents hydrogen and K" represents fluorine.

However, the general or preferred radical definitions or explanations presented above

BOs can also be combined with each other if desired, ie include combinations between respective ranges and preferred ranges. This applies both to final products and, accordingly, to precursors and intermediate products. In addition, individual definitions may not apply.

Preferred are compounds of formula (I) in which all radicals in each case have the preferred values indicated above.

Especially preferred are those compounds of formula (I) in which each of the radicals has particularly preferred values indicated above.

Illustrations of methods and intermediates

Pyrimidine derivatives of formula (I) can be prepared in various ways. At the initial stage, possible methods are schematically presented below. Unless otherwise specified, the radicals each have the meaning as above.

Scheme 1: Method A (EE, EE, Ne, VD" - hydrogen) o E d! E more) x-- 4 1 E 2 y Dest biv ! ho dz E Z

M M

-l Moss n) (PS) (-a)

Scheme 2: Method B (EE - hydrogen)

In in? Y vv E on no x-v

Av 4 7 1 and y---v v v x Z E and E i-Ot ! --I-, in: in in vv M 2 o My

Moss, M ) (M) OP-B)

Nai is a halogen.

Scheme 3: Method C (B, KE - hydrogen) in? in de E vnv s 9 Vg Y o De Y 4 E

J DN and J y

E and He dz i

Moss Moss (MI) (Pp) (U)

In in? r 4 no U v v' x E vA-m v? in' (UP) d - Y

Mach, them (I-s)

M is a metal

Scheme 4: Method Y 6 5 E 6 5 E no M Where is it Where is it? d3 R in--nai! in in? in and d- --2 in 7 ! 7 of them

Moss (-5) ih) Moss (1-a)

Ka is alkyl, trimethylsilyl, formyl or acetyl

On! is chlorine or bromine.

The preferred radical definitions for the formulas and equations above and below have already been presented above. These definitions apply not only to the final products of formula (1), but also to all intermediate compounds.

Method A

Some of the oxirane derivatives of formula (II), which are required as starting materials for the implementation of method A according to the invention, are known and can be prepared according to known methods (cf. OB-A 31 11 238 and EP-A 0 157 712).

A new and similar part of the object of this application is the oxirane derivatives of formulas (II-a) and IF) - (P-a). in;

M in which

Vya is in each case optionally substituted alkenyl, alkynyl or aryl.

B'X preferably represents in each case an optionally branched Cg2-Cv-alkenyl,

C2-Cv-haloalkenyl, C2-Cv-alkynyl, C2-Cv-haloalkynyl, and also represents phenyl, which is optionally mono- - trisubstituted by halogen or C1i-C4-alkyl.

ВЯ especially preferably represents in each case an optionally branched Ж-

C3-C5-alkenyl, C3-C5-haloalkenyl, C3-C5-alkynyl, C3-C5-haloalkynyl, and also represents phenyl, which can be mono- or disubstituted with halogen.

B'"I most preferably represents 2-propenyl (prop-2-en-1-yl), 1-propynyl (prop-1-yn-1-yl), (ZE)-4-chloro-2-methylbut- 3-en-2-yl, 2, 4-difluorophenyl.

Vya is particularly preferably 2-propenyl, 1-propynyl, 2, 4-difluorophenyl. (Thio)phenols of formula (I) are known or can be prepared according to known methods.

Method A according to the invention is carried out in the presence of a diluent and, if appropriate, in the presence of a base. If appropriate, an acid or a metal salt is then added to the resulting compound of formula (I-a) (see below).

Suitable diluents for the reaction according to the invention are all organic solvents that are inert. They preferably include alcohols such as, for example, ethanol and methoxyethanol; ketones such as, for example, 2-butanone; nitriles such as, for example, acetonitrile; esters, such as, for example, ethyl acetate; ethers, such as, for example, dioxane; aromatic hydrocarbons such as, for example, benzene and toluene; or amides such as, for example, dimethylformamide.

Suitable bases for the reaction according to the invention are all organic and inorganic bases that are commonly used. They preferably include alkali metal carbonates, such as, for example, sodium carbonate or potassium carbonate; alkali metal hydroxides, such as, for example, sodium hydroxide; alkali metal alcoholates, such as, for example, sodium methylate and potassium methylate and sodium ethylate and potassium ethylate; alkali metal hydrides, such as, for example, sodium hydride; and also lower tertiary alkylamines, cycloalkylamines and aralkylamines, such as, in particular, triethylamine. The use of sodium hydride is particularly preferred.

When carrying out method A according to the invention, the reaction temperatures can vary in a relatively wide range. In general, the method is carried out at temperatures in the range from 0 °C to 200 °C, preferably from 60 °C to 150 °C.

If appropriate, the reaction according to the invention can be carried out under elevated pressure. In general, the reaction is carried out in the range from 1 to 50 bar, preferably in the range from 1 to 25 bar.

When carrying out method A according to the invention, preferably from 1 to 2 mol of (thio)phenol of formula (II) and, if appropriate, from 1 to 2 mol of base is used per mol of oxirane of general formula (II). Isolation of final products is carried out in a generally accepted way.

Method B

Some ketones of the formula (IM), which are required as starting materials for carrying out method B according to the invention, are known.

A new and similar part of the object of this invention are ketones of the formula (IM-а) вв 5В Е 18 M uv v v uhvo (Ma) wa di o in which

XV represents 0,

B'B is in each case optionally substituted C2-C4-alkyl, alkenyl, alkynyl or cycloalkyl,

B2c Its 3B are the same or different and represent in each case hydrogen, halogen, cyano, nitro, OH, 5H, CH(-MoO-alkyl), C(alkyl)/"-MO-alkyl), C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C8-C-alkenyl,

C2-C4-haloalkenyl, C2-C4-alkynyl, Co-C--haloalkynyl, C-C4-alkylsulfinyl, C-C4-haloalkylsulfinyl, C1-Ca-alkylsulfonyl, C1-C--haloalkylsulfonyl, formyl, C2-Sv -alkylcarbonyl, C2-Cv-haloalkylcarbonyl, Co-C5-alukoxycarbonyl, Co-C5-haloalkyloxycarbonyl, C3-Cv-alkenyloxy, C3-Cv-alkynyloxy, C5-Cv-alkylcarbonyloxy, C2-Cv-haloalkylcarbonyloxy, trialylsilyl, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with halogen, C1-

Ca-alkyl, C-C-haloalkyl, C-C4-alkoxy or C2-C4-alkylcarbonyl,

XV represents O, 5, 50 or 50",

BB is hydrogen, fluorine, chlorine or C:-C4--haloalkyl,

Ko) BB and EB are the same or different and in each case represent hydrogen, halogen or optionally substituted alkyl, or together represent the group -СНо-СНео- so that, together with the carbon atom to which they are attached, form a cyclopropyl ring,

XV is mostly 0.

B'8 preferably represents in each case an optionally branched C2-Ca-alkyl, Co-

C4-haloalkyl, C2-Cv-alkenyl, C»-Cv-haloalkenyl, C2-Cv-alkynyl, C2-Cv-haloalkynyl, C1-C--alkoxy-

C2-C3-alkyl, C1-C4-haloalkyl-C2-C3-alkyl, tri(C1-C3-alkyl)silyl-C2-C3-alkyl, is a C3-

C;-cycloalkyl or C3-C7-cycloalkyl-Ci-C3-alkyl, each of which can be substituted in the cycloalkyl component by halogen, C-C-alkyl, C-C--haloalkyl, C-C-alkyl, C1- C4- haloalkoxy, C1-C4-haloalkylthio, C1-C4-alkylthio or phenoxy (which, in turn, can be substituted by halogen or C1-C4-alkyl).

B'B especially preferably represents in each case an optionally branched C2-

Ca-alkyl, Co-C4-haloalkyl, C3-C5-alkenyl, C3-C5-haloalkenyl, C3-C5-alkynyl, C3-C5-haloalkynyl, C1-

C3-C3-Alkoxy-Ethyl, C1-C3-Halo-Alkoxy-Ethyl, Tri(C1C-C6-Alkyl)silylethyl, is C3-C8-cycloalkyl or C3-C8-cycloalkyl-Ci-Co-alkyl, each of which can be substituted in the cycloalkyl component, halogen, C-C-alkyl, C-C-haloalkyl, C-i-C-haloalkyl,

C-C-Alkoxy, C-C4-haloalkylthio, C-C4-alkylthio or phenoxy (which, in turn, may be substituted by fluorine, chlorine, bromine or C-C4-alkyl).

B'B8 is most preferably tert-butyl, isopropyl, 2-propenyl (prop-2-en-1-yl), 1-propynyl (prop-1-yn-1-yl), cyclopropyl, 1-chlorocyclopropyl, 1 -fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl, 1-methylthiocyclopropyl, 1-trifluoromethylcyclopropyl, 1-phenoxycyclopropyl, 1-(2-chlorophenoxy)cyclopropyl, 1-(2-fluorophenoxy)cyclopropyl, 1-(4-fluorophenoxy)cyclopropyl, 1-(2,4-difluorophenoxy)cyclopropyl, (ZE)-4-chloro-2-methylbut-3-en-2-yl, cyclopropylmethyl.

BZ is particularly preferably tert-butyl, isopropyl, 2-propynyl, 1-propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl.

B28 and ZB are the same or different and preferably each represents hydrogen, halogen, cyano, nitro, CH(-MO(C1-Cv-alkyl)), C(C1-Cv-alkyl(-MO(C1-Cv-alkyl) ), C3-C6-cycloalkyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkyl, C6-C4-haloalkyl, C6-C4-haloalkylthio, C6-C4-haloalkylthio, C6-C4-alkenyl ,

С2-Са-alkynyl, СС-Са-alkylsulfinyl, СС-С--alkylsulfonyl, С2-Св5-alkylcarbonyl, /С2-Св5- alkoxycarbonyl, С3-Св-alkenyloxy, С3-Св-alkynyloxy, С2-Св5-alkylcarbonyloxy, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by halogen, C1-

Ca-alkyl, C-C-haloalkyl, C-C4-alkoxy or C2-C4-alkylcarbonyl.

В2В Its ЗВ are the same or different and especially preferably each represents hydrogen, halogen, cyano, nitro, CH(I-MO(C1-Ca-alkyl)), C(C1-Ca-alkyl).(-MO(Si- Ca-alkyl)), C3-Cv-cycloalkyl,

Ci-Ci-alkyl, Ci-Ci-Co-haloalkyl, Ci--Ci-Alkoxy, Ci-Ci-haloalkyl, Ci-C2-alkylthio, /Ci-C2-haloalkylthio, Ci-Ci-Alkylsulfinyl, Ci-Ci- alkylsulfonyl, acetyl, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C6-alkoxy, acetyl.

BB and ZB are the same or different and most preferably each represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, CH(-MOMe), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl, ethyl, n-propyl, isopropyl , n-, i-. c- or tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, difluorochloromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, or in each case optionally fluoro-, chloro-, bromo-, iodo-, methyl- , ethyl-, trifluoromethyl-, trichloromethyl-, difluoromethyl-, dichloromethyl-, difluorochloromethyl-, methoxy-, acetyl-monosubstituted phenyl, phenoxy or phenylthio.

B2b and ZB are especially preferably hydrogen. uv is preferably O or 5. uv is particularly preferably 0. uv is also particularly preferably 5.

B8 is preferably hydrogen, fluorine, chlorine or C-C0-haloalkyl.

Zo B"8 is particularly preferably hydrogen, fluorine, chlorine, difluoromethyl, trifluoromethyl or difluorochloromethyl.

BB is most preferably hydrogen, fluorine or chlorine.

VZV and BV are the same or different and preferably each represents hydrogen, fluorine, chlorine, bromine, iodine, C-C4-alkyl or C-C--haloalkyl, or together represent the group -"СН"-СНе-.

IN? and 25 are the same or different and especially preferably each represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl, or together represent the group -"СН2-СНе-".

BB and 288 are the same or different and most preferably each represents hydrogen or methyl, or together represent the group -СН2-СНе-.

A new and similar part of the object of this invention are ketones of the formula (IM-B) where E ac is 8-4 in br s (M-c) where to (c) in which

ХУ represents 5, 50, 50",

R is in each case optionally substituted alkenyl, alkynyl or cycloalkyl.

Vo and Zo are the same or different and represent in each case hydrogen, halogen, cyano, nitro, OH, 5H, CH(-MoO-alkyl), C(alkyl)/"-MO-alkyl), C3-SU-cycloalkyl, C1-C4-haloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C8-C-alkenyl,

C2-C4-haloalkenyl, C2-C4-alkynyl, C-C-haloalkynyl, C-C4-alkylsulfinyl, C-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, formyl, C2g-C5 -alkylcarbonyl, C2-Cv-haloalkylcarbonyl, C2-Cv-haloalkylcarbonyl, Cg-C5-haloalkyloxycarbonyl, C3-Cv-alkenyloxy, C3-Cv-alkynyloxy, Cg-Cv-alkylcarbonyloxy, C2-Cv-haloalkylcarbonyloxy, trialkylsilyl, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with halogen, C1-

Ca-alkyl, C-C-haloalkyl, C-C4-alkoxy or C2-C4-alkylcarbonyl,

Us represents 0, 5, 50 or 50",

B" represents hydrogen, fluorine, chlorine or C1-Ca4-haloalkyl,

All and es are the same or different and represent in each case hydrogen, halogen or optionally substituted alkyl, or together represent the group -СНо-СНео- so that, together with the carbon atom to which they are attached, they form a cyclopropyl ring,

ХУ is mostly 5.

ВЭ is preferably in each case an optionally branched Cg2-Cv-alkenyl,

C2-Cv-haloalkenyl, C2-Cv-alkynyl, Co-Cv-haloalkynyl, is C3-C7-cycloalkyl, which can be substituted in the cycloalkyl component by halogen, C-C-alkyl, C-C4-haloalkyl, C1-

C-Alkoxy, C-C-halo-Alkoxy, C:1-C--haloalkylthio, C-C--Alkylthio or phenoxy (which, in turn, can be substituted by halogen or C-C4-alkyl).

ВЕ especially preferably represents in each case an optionally branched Сз-

C3-C5-haloalkenyl, C3-C5-alkynyl, C3-C5-haloalkynyl, is C3-C6-cycloalkyl, which can be substituted in the cycloalkyl component by halogen, C:i-Ca-alkyl, C1-C4 - haloalkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkylthio, C-C4-alkylthio or phenoxy (which, in turn, can be replaced by fluorine, chlorine, bromine or C-C- alkyl).

VE is most preferably 2-propenyl (prop-2-en-1-yl), 1-propynyl (prop-1-yn-1-yl), cyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl , 1-methoxycyclopropyl, 1-methylthiocyclopropyl, 1-trifluoromethylcyclopropyl, 1-phenoxycyclopropyl, 1-(2-chlorophenoxy)cyclopropyl, 1-(2-fluorophenoxy)cyclopropyl, 1-(4-fluorophenoxy)cyclopropyl, 1-(2, 4 -difluorophenoxy)cyclopropyl, (ZE)-4-chloro-2-methylbut-3-en-2-yl.

VAE is particularly preferably 2-propenyl, 1-propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl. dgs and BZ are the same or different and preferably each represents hydrogen, halogen, cyano, nitro, CH(I-MO(C:1-Cv-alkyl)), C(C1-Cv-alkyl (MO(C1-Cv- alkyl)), C3-Cv-cycloalkyl, C1-Ca-alkyl, C1-

Са4-haloalkyl, Сі-С--аlkoxy, Сі-С--haloаlkoxy, Сі-С4-alkylthio, Сі--С4--haloalkylthio, Сге-С--alkenyl, 0 С2-Са-alkynyl, Сі-Сл- alkylsulfinyl, C2-C4-alkylsulfonyl, C2-C6-alkylcarbonyl, /C2-C6- alkoxycarbonyl, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C2-C5-alkylcarbonyloxy, or is phenyl, phenoxy or phenylthio, each of which are optionally monosubstituted by halogen, C1-

Ca-alkyl, C-C-haloalkyl, C-C4-alkoxy or C2-C4-alkylcarbonyl.

Hgs and all are the same or different and especially preferably each represents hydrogen, halogen, cyano, nitro, CH(I-MO(C1-Ca-alkyl)), C(C1-Ca-alkyl).(-MO(Si- Ca-alkyl)), C3-Cv-cycloalkyl,

Ci-Ci-alkyl, Ci-Ci-Co-haloalkyl, Ci--Ci-Alkoxy, Ci-Ci-haloalkyl, Ci-C2-alkylthio, /Ci-C2-haloalkylthio, Ci-Ci-Alkylsulfinyl, Ci-Ci- alkylsulfonyl, acetyl, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, or are phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C6-alkoxy, acetyl.

Vo and all are the same or different and most preferably each is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, CH(-MOMe), cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl, ethyl, n-propyl, isopropyl , n-, i-. c- or tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, difluorochloromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio, difluoromethylthio, or in each case optionally fluoro-, chloro-, bromo-, iodo-, methyl- , ethyl-, trifluoromethyl-, trichloromethyl-, difluoromethyl-, dichloromethyl-, difluorochloromethyl-, methoxy-, acetyl-monosubstituted phenyl, phenoxy or phenylthio.

B2C and 83 are especially preferably hydrogen. Ue is preferably 0 or 5. Ue is especially preferably 0. U is also especially preferably 5.

B"E is preferably hydrogen, fluorine, chlorine or C1i-C2o-haloalkyl.

BC is particularly preferably hydrogen, fluorine, chlorine, difluoromethyl, trifluoromethyl or difluorochloromethyl.

BS is most preferably hydrogen, fluorine or chlorine. dos and Bc are the same or different and preferably each represents hydrogen, fluorine, chlorine, bromine, iodine, C-C4-alkyl or C-C--haloalkyl, or together represent the group -"СН2-СНе-".

Weight and weight are the same or different and especially preferably each is hydrogen,

fluorine, chlorine, methyl, ethyl or trifluoromethyl, or together represent the group -СН2-СНе-.

Ves and des are the same or different and most preferably each represents hydrogen or methyl, or together represent the group -СН2-СНе-.

Ketones of the formula (IM) can be obtained using a known method (cf. EP-A 0 040 345, EP-A 0 001 399). Ketones of the formula (IM) are obtained, for example, using the following method:

Scheme 5: Method E (ХО, 5) в' в? E vd E x-- z» Kf x-v she nya - y -

Her He dz and He dz (X) (XI) aX)

Nai is a halogen.

Halides of formula (X) are known. In formula (X), Na! preferably represents chlorine or bromine.

Method E according to the invention is carried out in the presence of a diluent and in the presence of an inorganic base.

Suitable diluents for the reaction according to the invention are all organic solvents that are inert. They preferably include ketones, such as, for example, acetone and 2-butanone; nitriles such as, for example, acetonitrile; esters, such as, for example, ethyl acetate; ethers, such as, for example, dioxane; aromatic hydrocarbons such as, for example, benzene and toluene; or chlorinated hydrocarbons such as, for example, dichloromethane.

Suitable bases for the reaction according to the invention are all organic and inorganic bases that are commonly used. They preferably include alkali metal carbonates, such as, for example, sodium carbonate or potassium carbonate; alkali metal hydroxides, such as, for example, sodium hydroxide; alkali metal alcoholates, such as, for example, sodium methylate and potassium methylate and sodium ethylate and potassium ethylate; alkali metal hydrides, such as, for example, sodium hydride; and also lower tertiary alkylamines, cycloalkylamines and aralkylamines, such as, in particular, triethylamine. The use of sodium hydride is particularly preferred.

In method B according to the invention, the reaction temperatures can vary within a certain range. In general, the method is carried out at temperatures in the range from 50 "C to 150 "C, preferably from 20 "C to 100 76.

The reaction according to the invention is preferably carried out in an inert gas, such as, in particular, nitrogen or argon.

When carrying out method E according to the invention, halides of formula (X) and (thio)alcohols

From the formula (XI) is used in approximately equimolar amounts; however, it is also possible to use above or below this ratio up to about 20 mole percent.

The inorganic base is advantageously used in an excess of 5 to 75 mol percent, preferably 10 to 50 mol percent.

Pyrimidinyl halides of formula (M), which are also required as starting materials for carrying out method B according to the invention, are known.

Method B according to the invention is carried out in the presence of a diluent and in the presence of an organic alkali metal compound. If appropriate, an acid or metal salt is then added to the resulting compound of formula (I-B) (see below).

Preferred diluents for the reaction according to the invention are inert organic solvents. They preferably include those with a low freezing point, such as, in particular, ethers such as diethyl ether or tetrahydrofuran. Treatment with mixtures of these two ethers is preferred.

Preferred alkali metal organic compounds used for the reaction according to the invention are alkali metal alkyls, such as, especially, n-butyllithium; however, alkali metal aryls such as phenyllithium can also be used.

In the method according to the invention, the reaction temperatures can vary within a certain range. In general, the method is carried out at temperatures in the range from -150 "C to - "C, preferably from -120 "C to -80 70.

The reaction according to the invention is preferably carried out in an inert gas, such as, in particular, nitrogen or argon.

When carrying out the method according to the invention, ketones of the formula (IM) and halides of the formula (M) are used in approximately equimolar amounts; however, it is also possible to use above or below this ratio up to about 20 mole percent. The alkali metal organic compound is advantageously used in an excess of 5 to 75 mol percent, preferably up to 50 mol percent.

In this case, the alkali metal organic compound can be initially allowed to react with the halide of formula (M), and then the keto compound of formula (IM) can be added; 10, however, it is also possible to initially charge the keto compound and the halide and then add the alkali metal organic compound at a low temperature (for example, from -100 C to -130 C). Isolation of compounds of the formula (I-B) is carried out by hydrolysis, with water, alkali metal alcoholate (for example, lithium alcoholate) is initially formed in the reaction. After that, additional processing is carried out in a generally accepted way.

Method C

Some bromides of the formula (MI) are known. A new and similar part of the object of this invention are bromides of the formula (MI-a) o B dv» -Oe (MI-a) xx. in

M in which

B is halogen or substituted alkyl,

Be is halogen or substituted alkyl,

BA and BA are the same or different and preferably each represents fluorine, chlorine, bromine, iodine or C-C4-haloalkyl, or together represent the group -"СН"-СНе-.

A and BBA are the same or different and especially preferably each represents fluorine, chlorine or trifluoromethyl, or together represent the group -СН»-СНе-.

BA and BA are the same or different and most preferably together represent the group -СНе-

СНе-. (thio)phenols of formula (III) are also known (see above for Method A).

Some ketones of the formula (MII), which occur as intermediate compounds for the implementation of method C according to the invention, are known.

Organometallic compounds of the formula (MI) are known, where M in the formula (MI!) is mostly lithium or magnesium.

Method C (stage 1) according to the invention is carried out in the presence of a diluent and, if appropriate, in the presence of a base. Suitable diluents for the reaction according to the invention are all organic solvents that are inert. They preferably include alcohols such as, for example, ethanol and methoxyethanol; ketones such as, for example, 2-butanone; nitriles such as, for example, acetonitrile; esters, such as, for example, ethyl acetate; ethers, such as, for example, dioxane; aromatic hydrocarbons such as, for example, benzene and toluene; amides such as, for example, dimethylformamide; or sulfoxides, such as, for example, dimethyl sulfoxide.

Suitable bases for the reaction according to the invention are all organic and inorganic bases that are commonly used. They preferably include alkali metal carbonates, such as, for example, sodium carbonate or potassium carbonate; alkali metal hydroxides, such as, for example, sodium hydroxide; alkali metal alcoholates, such as, for example, sodium methylate and potassium methylate and sodium ethylate and potassium ethylate; alkali metal hydrides, such as, for example, sodium hydride; and also lower tertiary alkylamines, cycloalkylamines and aralkylamines, such as, in particular, triethylamine.

When carrying out method C according to the invention, the reaction temperatures can vary in a relatively wide range. In general, the method is carried out at temperatures in the range from 0 °C to 200 °C, preferably from 20 °C to 100 °C.

If appropriate, the reaction according to the invention can be carried out under elevated pressure. In general, the reaction is carried out in the range from 1 to 50 bar, preferably in the range from 1 to 25 bar.

When carrying out method C (stage 1) according to the invention, more preferably 25 mmol

(thio)phenol of the formula (PI) and, if appropriate, from 75 to 112 mmol of the base are used for from 75 to 112 mmol of the bromoketone of the general formula (MI), in dimethyl sulfoxide as a solvent.

Isolation of final products is carried out in a generally accepted way.

Method C (stage 2) according to the invention is carried out in the presence of a diluent and in the presence of an organometallic compound. If appropriate, an acid or a metal salt is then added to the resulting compound of formula (I-c) (see below).

Preferred diluents for the conversion according to the invention of compounds of formula (MI) into compounds of formula (I-c) are inert organic solvents. They include, in particular, ethers such as diethyl ether or tetrahydrofuran; aromatic hydrocarbons such as, for example, benzene and toluene. Preferred organometallic compounds used for the reaction according to the invention are alkaline earth metal alkyls, especially methylmagnesium bromide; however, it is also possible to use alkali metal alkyls such as n-butyllithium.

In the method according to the invention, the reaction temperatures can vary within a certain range. In general, the method is carried out at temperatures in the range from -100 C to -20 C, preferably in the range from -78 C to 0 C.

The reaction according to the invention is preferably carried out in an inert gas, such as, in particular, nitrogen or argon.

When carrying out the method according to the invention, 2.5 mmol of the ketone of the formula (MI) is reacted with the organometallic compounds of the formula (MI) in an excess of 300 mol percent in toluene.

After that, additional processing is carried out in a generally accepted way.

In this case, the ketone (MI) can be initially charged, and then the organometallic compound of formula (MI) can be added at a suitable temperature (for example, 0 C).

Isolation of compounds of the formula (I-c) is carried out by hydrolysis, with water, metal alcoholate (for example, magnesium alcoholate) is initially formed in the reaction. After that, additional processing is carried out in a generally accepted way.

The method of Yu

Alcohol derivatives of the formula (I-Bb), necessary as starting materials for the implementation of method Y according to the invention, form part of the object of this invention and can be prepared according to methods A-C.

From Halides of formula (IX) are known.

The method of SE according to the invention is carried out in the presence of a diluent and, if appropriate, in the presence of a base. If appropriate, an acid or metal salt is then added to the resulting compound of formula (I-B) (see below).

Suitable diluents for the reaction according to the invention are all organic solvents that are inert. They preferably include ketones, such as, for example, acetone and 2-butanone; nitriles such as, for example, acetonitrile; esters, such as, for example, ethyl acetate; ethers, such as, for example, dioxane; aromatic hydrocarbons such as, for example, benzene and toluene; or chlorinated hydrocarbons such as, for example, dichloromethane.

Suitable bases for the reaction according to the invention are all organic and inorganic bases that are commonly used. They preferably include alkali metal carbonates, such as, for example, sodium carbonate or potassium carbonate; alkali metal hydroxides, such as, for example, sodium hydroxide; alkali metal alcoholates, such as, for example, sodium methylate and potassium methylate and sodium ethylate and potassium ethylate; alkali metal hydrides, such as, for example, sodium hydride; and also lower tertiary alkylamines, cycloalkylamines and aralkylamines, such as, in particular, triethylamine. The use of sodium hydride is particularly preferred.

When carrying out method O according to the invention, reaction temperatures can vary in a relatively wide range. In general, the method is carried out at temperatures in the range from -207 and 100 "C, preferably in the range from 0 "C to 60 "C.

If appropriate, the reaction according to the invention can be carried out under elevated pressure. In general, the reaction is carried out in the range from 1 to 50 bar, preferably in the range from 1 to 25 bar.

When carrying out method Y according to the invention, preferably from 1 to 2 mol of the halide of the formula (IX) and, if appropriate, from 1 to 2 mol of the base is used per mol of the alcohol of the general formula (I-b). Isolation of final products is carried out in a generally accepted way.

Compounds of the general formula (I) obtained by methods according to the invention can be converted into acid addition salts or complexes of metal salts.

For the preparation of physiologically acceptable acid addition salts of compounds of the general formula (I), the following acids are preferable: hydrohalic acids, for example, hydrochloric acid and hydrobromic acid, especially hydrochloric acid, and also phosphoric acid,

nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, for example, acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, and sulfonic acids, for example , p-toluenesulfonic acid and 1, 5-naphthalenedisulfonic acid.

Acid addition salts of compounds of general formula (I) can be obtained in a simple manner using conventional salt formation methods, for example, by dissolving a compound of general formula (I) in a suitable inert solvent and adding an acid, for example, hydrochloric acid, and can be isolated by a known method, for example, by filtering them, and can optionally be purified by washing them with an inert organic solvent.

Preferable for the preparation of complexes of metal salts of 65 compounds of the general formula (I) are metal salts of HER. - to them. of the main group and transition groups I and I of the periodic table, examples of which include copper, zinc, manganese, magnesium, tin, iron, and nickel.

Suitable anions for the salts are those which are preferably derived from the following acids: hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in addition phosphoric acid, nitric acid and sulfuric acid.

Complexes of metal salts of compounds of the general formula (I) can be obtained in a simple way using conventional methods, for example, by dissolving the metal in an alcohol, for example, ethanol, and adding the solution to the compounds of the general formula I. Complexes of metal salts can be isolated using known methods , for example, by filtration, and, if necessary, will be purified before crystallization.

The present invention also relates to a composition for combating undesirable microorganisms, which includes active compounds according to the invention. This composition is preferably a fungicidal composition that includes agriculturally acceptable auxiliary substances, solvents, carriers, surface-active substances or fillers.

In addition, the invention relates to a method of combating unwanted microorganisms, which differs in that the active compounds according to the invention are used on phytopathogenic fungi and/or their growth sites.

According to the invention, the carrier is a natural or synthetic organic or inorganic substance with which the active compounds are mixed or bound for better applicability, especially for application to plants or plant parts or seeds. The carrier, which may be solid or liquid, is generally inert and should be suitable for use in agriculture.

Suitable solid or liquid carriers include, for example, ammonium salts and natural inert borax, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and synthetic borax, such as finely divided silica, alumina, and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils, and their derivatives. It is also possible to use mixtures of such carriers. Suitable solid carriers for the granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic flours, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.

Suitable liquefied gaseous propellants or carriers are liquids which are gaseous at ambient temperature and atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

Tackifying agents such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the preparations. Additional auxiliary substances can be mineral and vegetable oils.

If the used extender is water, it is also possible to use, for example, organic solvents as auxiliary solvents. The liquid solvents used are mainly: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of mineral oils, mineral oils and vegetable oils, alcohols such as butanol or glycol and their simple and complex esters, ketones such as acetone, methyl ethyl ketone, or methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and also water.

Compositions according to the invention may contain other additional components, such as, for example, surface-active substances. Suitable surfactants are emulsifiers and/or foaming agents, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples of them are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalene sulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (mainly alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives ( mainly alkyl taurates), phosphoric esters of semi-ethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of compounds containing sulfates, sulfonates, and phosphates, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignosulfite spent alkali and methyl cellulose. The presence of a surface-active substance is necessary if one of the active compounds and/or one of the inert carriers are insoluble in water and if the application is carried out in water. The proportion of surfactants is in the range from 5 to 40 percent by weight of the composition according to the invention.

Dyes such as inorganic pigments such as iron oxide, titanium oxide and berlin azure, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace elements such as iron, manganese, boron, copper salts can also be used. , cobalt, molybdenum and zinc.

If it is appropriate, the presence of other additional components is also possible, for example, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestrants, complexing agents. In general, the active compounds can be combined with any solid or liquid excipient commonly used in the preparation of the drug.

Compositions and preparations according to the invention usually contain in the range from 0.05 to 99 95 by weight, 0.01 to 98 95 by weight, preferably from 0.1 to 95 95 by weight, especially preferably from 0.5 to 90 95 of active compounds, most preferably from 10 to 70 95 by weight.

The active compounds or compositions according to the invention can be used as such

Zo or, depending on their respective physical and/or chemical properties, in the form of their preparations or using forms prepared from them, such as aerosols, suspension capsules, concentrates obtained by refrigeration, concentrates obtained by heating, encapsulated granules, finely divided granules, liquid-flowable concentrates for seed treatment, ready-to-use solutions, powdered powders, emulsifying concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersed powders, oil-mixable liquid-flowable concentrates, oil-mixable liquids, foams, pastes , pesticide-coated seeds, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble seed treatment powders, wettable powders, natural products and synthetic substances impregnated with an active compound, as well as microencapsulation in polymeric substances iny and in seed coating materials, as well as obtained by cooling and obtained by heating of ultra-low volume preparations.

Said preparations can be prepared by a method known as reg 5e, for example, by mixing the active compounds with at least one conventional extender, solvent or diluent, emulsifier, dispersing agent, and/or binder or fixative, wetting agent, water repellent, if appropriate desiccants and UV-stabilizers and, if appropriate, dyes and pigments, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also other processing aids.

Compositions according to the invention include not only preparations that are already ready for use and can be applied with the help of a suitable device to a plant or seed, but also commercial concentrates that should be diluted with water before use.

Active compounds according to the invention can be present as such or in their (commercial) preparations and in application forms prepared from these preparations in the form of a mixture with other (known) active compounds, such as insecticides, attractants, sterilizers, bactericides, acaricides, nematicides , fungicides, growth regulators, herbicides, fertilizers, antidotes and/or chemical signaling substances.

Treatment of plants and parts of plants according to the invention with the help of active compounds or compositions is carried out directly or by exposure to their environment, places of residence or places for storage using generally accepted treatment methods,

for example, by dipping, spraying, atomizing, irrigating, vaporizing, dusting, fine-drop spraying, spreading, foaming, painting, distributing, wetting (infiltration), drip irrigation and, in the case of propagating material, especially in the case of seeds, also in the form of a powder for dry treatment of seeds, solution for treatment of seeds, water-soluble powder for semi-dry etching, by inlaying, by covering with one or several shells. It is also possible to apply the active compounds using the ultra-low volume method or to inject the preparation of the active compound or the active compound itself into the soil.

The invention also covers a method of treating seeds.

The invention also relates to seeds that have been treated according to one of the methods described in the previous paragraph. Seeds according to the invention are used in methods for protecting seeds from unwanted microorganisms. In these methods, seeds treated with at least one active compound according to the invention are used.

The active compounds or compositions according to the invention are also suitable for seed treatment.

Most of the damage to agricultural crops caused by pathogenic organisms is caused by seed infection during storage or after sowing, both before and after germination. This phase is particularly critical because the roots and shoots of the growing plant are extremely sensitive, and even a small injury can lead to the death of the plant. Therefore, there is an extreme interest in protecting the germinating plant seed with suitable compositions.

The fight against phytopathogenic fungi by treating plant seeds has been known for a long time and is constantly being improved. However, seed treatment causes a series of problems that cannot always be solved satisfactorily. For example, it would be desirable to develop methods of protecting germinating plant seeds that dispense with, or at least substantially reduce, the additional application of a crop protection composition after seeding or after plant germination. In addition, it is desirable to optimize the applied amount of the active compound in such a way as to provide optimal protection for the germinating plant seeds against the attack of phytopathogenic fungi, but without damaging the plant itself by means of the applied active compound itself. Especially, methods of processing seeds should also take into account the inherent

Fungicidal properties of transgenic plants to achieve optimal protection of seeds, germinating plants 3 with minimal use of compositions for the protection of agricultural crops.

Therefore, the present invention also relates to a method of protecting seeds of germinating plants from the attack of phytopathogenic fungi by treating seeds with the composition according to the invention.

The invention also relates to the use of the composition according to the invention for treating seeds to protect germinating plant seeds from phytopathogenic fungi. In addition, the invention relates to seeds treated with compositions according to the invention for protection against phytopathogenic fungi.

Control of phytopathogenic fungi, which affect plants after germination, is carried out mainly by treating the soil and aerial parts of plants with compositions for the protection of agricultural crops. Taking into account the possible impact of means for the protection of agricultural crops on the environment and human and animal health, attempts are made to reduce the applied amounts of active compounds.

One of the advantages of this invention is that the specific systemic properties of the active compounds and compositions according to the invention mean that the treatment of seeds with the help of these active compounds and compositions not only protects the seeds themselves, but also the plants obtained after germination from phytopathogenic fungi. Thus, it is possible to do without direct treatment of the agricultural crop during germination or soon after.

It should also be taken into account that the active compounds or compositions according to the invention can be used in particular also for transgenic seeds, in which case the plant that grows from such seeds is able to express a protein that acts on pests.

By treating such seeds with active compounds or compositions according to the invention, only the expression of a protein, for example, an insecticidal protein, can control certain pests.

Unexpectedly, in this case, a further synergistic effect can be observed, which additionally increases the effectiveness of protection against pest attacks.

Compositions according to the invention are suitable for seed protection of any type of plant used in agriculture, greenhouses, forestry or horticulture and viticulture. This is especially true for cereal seeds (such as wheat, barley, rye, triticale, sorghum/millet and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, and beets (such as sugar beets and fodder beets ), peanuts, oilseed rape, poppy, olives, coconut,

cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onion and lettuce), turf and ornamental plants (see also in this application below). The treatment of cereal seeds (such as wheat, barley, rye, triticale and oats), corn and rice is extremely important.

As also described below, treatment of transgenic seeds with active compounds or compositions according to the invention is particularly essential. This refers to plants containing at least one heterologous gene that enables the expression of a polypeptide or protein having insecticidal properties. A heterologous gene in a transgenic seed can originate, for example, from microorganisms of the species Vasiyi5, KPi2obisht, Rzeidotopa, Ze!itaya,

Tiispodegta, Siamirasieg, Siotiv5 or Siyosiadisht. This heterologous gene is predominantly of Vasiyya5 5 origin, in which case the gene product is effective against the corn moth and/or the western corn beetle. Most preferably, the heterologous gene originates from Vasiyz IpPyhipdiepvyv.

In the context of this invention, the composition according to the invention is applied to the seed either alone or in a suitable preparation. Preferably, the seed is processed in a state in which it is suitable enough that no damage occurs during processing. In general, seeds can be treated at any time between harvest and sowing.

It is generally accepted to use seeds that have been separated from the plant and freed from seeds, shells, stems, skin, hairs or fruit pulp. Thus, it is possible to use, for example, seeds that have been collected, cleaned and dried to a moisture content of less than 15595 by weight. Alternatively, it is also possible to use seeds which, after drying, have, for example, been treated with water and then dried again.

When treating seeds, special attention should be paid to the amount of the composition according to the invention that is applied to the seed and/or the amount of additional auxiliaries chosen in such a way as not to have a negative effect on seed germination or so that the resulting plant is not damaged. This must be especially ensured in the case of active compounds that may exhibit phytotoxic effects at certain application rates.

Compositions according to the invention can be applied directly, that is, they may not contain any other components and are undiluted. In general, application is preferred

From compositions for seeds in the form of suitable preparations. Suitable preparations and methods of seed treatment are known to specialists in this field of technology and are described, for example, in the following documents: О5 4272417 А, 005 4245432 А, 05 4,808,430 А, 005 5,876,739 А, 05 2003/0176428 AT, MO 2002/080675 AT, MO 2002/028186 Ag.

The active compounds that can be used according to the invention can be transformed into conventional preparations for seed treatment, such as solutions, emulsions, suspensions, powders, foams, suspensions or other compositions for coating seeds, and also OM preparations.

These preparations can be prepared in a generally known manner, by mixing the active compounds with generally accepted auxiliary substances, such as, for example, generally accepted fillers and also solvents or thinners, dyes, wetting agents, dispersing agents, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.

The dyes that may be present in seed dressings that can be used according to the invention are all dyes that are commonly used for these purposes. In this context, it is possible to use not only pigments that are poorly soluble in water, but also dyes that are soluble in water. Examples include dyes known under the names Kpodatipe B, S.I. Ridtepi Kea 112 ii S.I. Zoimepi Kea 1.

Suitable wetting reagents which may be present in seed dressings which may be used in accordance with the invention are all substances which promote wetting and which are generally used for the preparation of agricultural preparations of active compounds. Predominantly used are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Suitable dispersing agents and/or emulsifiers that may be present in seed dressings that may be used in accordance with the invention are all nonionic, anionic and cationic dispersing agents commonly used in the preparation of active compound agricultural preparations. Predominantly used are nonionic or anionic dispersing agents or mixtures of nonionic or anionic dispersing agents. Suitable dispersing agents include, in particular, ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and their phosphated or sulfated derivatives. Suitable anionic dispersing agents are, in particular, lignosulfonates, salts of polyacrylic acid, and arylsulfonate/formaldehyde condensates.

The antifoam agents that may be present in the seed dressings that can be used according to the invention are all substances that inhibit the formation of foam, which are generally used for the preparation of agricultural preparations of active compounds. Silicone antifoams and magnesium stearate are mainly used.

Preservatives that can be present in seed dressings that can be used according to the invention are all substances that can be used for these purposes in agricultural compositions. Dichlorphen and benzyl alcohol semiformal can be mentioned as an example.

Secondary thickeners, which may be present in seed dressings used according to the invention, are all substances suitable for these purposes in agricultural compositions. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clay and finely divided silicon dioxide are preferred.

Adhesives that may be present in the seed treatment preparations used in accordance with the invention are all commonly used binders used in seed treatment products. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose can be mentioned as preferred.

Gibberellins, which can be present in preparations for treating seeds used according to the invention, can preferably be gibberellins At, AZ (- gibberellic acid), A4 and A7; the use of gibberellic acid is especially preferred.

Gibberellins are known (cf. K. Uuedieg "Spetiye deg Rpaplep5sptsi2-ypa 5spaaiiiipd5bekatriipd5 te!"

Chemistry of compositions for the protection of agricultural crops and pesticides), volume 2, Zrhipdeg

Mepad, 1970, p. 401-412).

Preparations for seed treatment that can be used according to the invention can be used to treat a wide range of seeds, including seeds of transgenic plants, either directly or by pre-dilution with water. In this context, additional synergistic effects may also occur in cooperation with substances formed by expression.

All mixers which may be conventionally used for the seed treatment operation are suitable for treating the seed with the seed treatment preparations which may be used in accordance with the invention or with preparations prepared therefrom by the addition of water. Specifically, the seed treatment procedure consists of placing the seed in a mixer, adding the preferred amount of the seed treatment, either as such or after pre-dilution with water, and mixing until the drug is homogeneously distributed on the seed. If it is expedient, then a drying operation is carried out after that.

The active compounds or compositions according to the invention have strong microbicidal activity and can be used to control unwanted microorganisms such as fungi and bacteria, to protect agricultural crops and to protect materials.

Fungicides can be used to protect agricultural crops against Riachtoadiorpogoptusei, Ootusei5, Sppuigidiotusei5z, 2udotusesi5z, Azsotusei5,

Vazidiotuseisez and Oeshegotuseiyev.

Bactericides can be used to protect agricultural crops against Rztepdotopadaceae, Rpi2gobiaceae, Epiegorasiegiaceae, Sogupebasiegiaceae and Zigeriotuseiaceae.

Fungicidal compositions according to the invention can be used for therapeutic or protective control of phytopathogenic fungi. In addition, the invention also relates to therapeutic and protective methods of combating phytopathogenic fungi by using active compounds or compositions according to the invention, which are applied to seeds, plants or parts of plants, fruits or soil in which plants grow.

Compositions according to the invention for combating phytopathogenic fungi for the protection of agricultural crops include an effective, but not phytotoxic, amount of active compounds according to the invention. "Effective, but not phytotoxic amount" means the amount of the composition according to the invention, which is sufficient to control the fungicidal disease of the plant in a sufficient manner or to completely eradicate the fungicidal disease, and which, at the same time, does not cause any symptoms of phytotoxicity. In general, this application rate can vary within a relatively wide range. It depends on many factors, for example, the fungus to be combated, the plant, the climatic conditions and the components of the 60 compositions according to the invention.

The fact that active compounds are well tolerated by plants in the concentrations necessary to combat plant diseases makes it possible to treat aerial parts of plants, reproductive stock and seeds, and soil.

All plants and plant parts can be treated according to the invention. By plants in this application is meant all plants and plant populations, such as desirable and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants). Agricultural crops can be plants that can be obtained by conventional breeding and optimized methods or by means of biotechnology and genetic engineering methods or combinations of these methods, including transgenic plants and including plant cultivars that are protected and unprotected by plant breeders' rights. Plant parts include all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which are leaves, needles, peduncles, stems, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes.

Plant parts also include harvested material and vegetative and generative propagating material, such as petioles, tubers, rhizomes, shoots and seeds.

The active compounds according to the invention are suitable for protecting plants and plant organs, for increasing harvested crops, for improving the quality of harvested crops, as they are well tolerated by plants, have favorable toxicity to warm-blooded species and do not harm the environment. They can mainly be used as agents for the protection of agricultural crops. They are effective against normally sensitive and resistant species and against all or some stages of development.

Plants that can be processed in accordance with the invention include the following major cultivated plants: corn, soybeans, cotton, oilseeds and oilseeds such as

Vgazzisa pari5 (e.g. Sapoia), Vgazzisa gara, V. |ipsea (e.g. (field) mustard) and

Vgazvisa sagipaga, rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, grapes and various fruits and vegetables from different botanical taxa, for example, Kozaseae 5yr. (for example, pome fruits such as apples and pears, as well as stone fruits such as apricots, cherries, almonds and peaches, and berries such as strawberries), Kirevsioidae 5yr.,

Uydiapdaseae sr., Veishiaseae 5r., Apasagaiaseae 5r., Radaseae 5r., Mogaseae 5r., OiIeaseae sr.,

From Asiapidaseae 5 years, Iaigaseae 5 years, Myzaseae 5 years. (e.g. banana trees and plantations),

Kibiaseye 5 years. (for example, coffee), Tpeaseae 5r., Ziegotsiiseae 5r., Kshaseae 5r. (for example, lemons, oranges and grapefruit); ZoiIapaseae 5 years. (for example, tomatoes, potatoes, peppers, eggplants), I yPyaseae 5 years, Sotroziae 5 years. (for example, lettuce, artichoke and chicory - including chicory root, chicory-endive or common chicory), ShtbeyYegaye 5r. (for example, carrots, parsley, celery and celeriac), Sysygriaceae sr. (for example, cucumbers - including gherkins, pumpkin, watermelon, bottle gourd and cantaloupe), AIPShaseee 5 years. (eg leeks and onions)

Sgisitegaye 5 years. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radish, horseradish, watercress, and Chinese cabbage), Hedytypozaye 5yr. (for example, peanuts, peas, and beans - for example, common beans and horse beans), Speporodiaceae 5 years. (for example, leaf beet, fodder beet, spinach, beet),

Maimaseae (e.g. okra), Azragadaseae (e.g. asparagus); useful plants and decorative plants in the garden and wood; and in each case genetically modified types of these plants.

As already indicated above, it appears possible to process all plants and their parts according to the invention. In a preferred embodiment, plants of wild species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or cross-linking of protoplasts, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are processed. The term "parts" or "plant parts" or "plant parts" has been described above. More preferably, plants of plant cultivars, which are commercially available or used, are treated according to the invention. Cultivars of plants are understood as plants that have new properties ("characteristics") and were obtained with the help of generally accepted selection, by mutagenesis or by recombinant DNA technologies. They can be cultivars, varieties, bio- or genotypes.

The processing method according to the invention can be used to process genetically modified organisms (GMOs), for example, plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene that is provided or assembled outside the plant and, when introduced into a nuclear, chloroplast, or mitochondrial gene, provides the transformed plant with new or improved agronomic or other properties by expression of the protein or polypeptide of interest, or by downregulation or silencing of other gene(s) present in the plant (using, for example, antisense technology, cosuppressive technology or RNAi and RNA interference technology). A heterologous gene that is present in the genome is also called a transgene. A transgene that is defined by its specific localization in the plant genome is called a transformational or transgenic event.

Depending on the types of plants or plant cultivars, their localization and growth conditions (soil, climate, growing season, nutrition), processing according to the invention can also lead to superadditive ("synergistic") phenomena. Thus, for example, reduced application rates and/or a wider spectrum of activity and/or increased activity of the active compounds and compositions that can be used according to the invention are possible, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or salt content in the soil, increased flowering, earlier harvest, faster ripening, higher yield, larger fruits, higher plant height, greener leaf color, earlier flowering, better quality and/or higher nutritional value of harvested products, higher sugar concentration in the fruit, better storage stability and/or processing ability of the harvested products, which exceed the effects that are actually supposed to be obtained.

At certain application rates, combinations of active compounds according to the invention can also have an enhanced effect on plants. Thus, they are suitable for mobilizing the plant's defense system against the attack of unwanted phytopathogenic fungi and/or microorganisms and/or viruses. This can be, if appropriate, one of the reasons for increasing the activity of the combinations according to the invention, for example, in relation to fungi. Substances that strengthen plants (induce resistance) in the context of this invention also mean those substances or combinations of substances that are able to stimulate the defense system of plants in such a way that upon subsequent inoculation of an unwanted phytopathogenic fungus, the treated plants show a sufficient degree of resistance to of these undesirable phytopathogenic fungi. Thus, substances according to the invention can be used to protect plants against the attack of the above-mentioned pathogens within a certain period of time after treatment. The period during which protection is achieved usually lasts from 1 to 10 days, preferably from 1 to 7 days, after treatment of plants with active compounds.

Plants and plant varieties that are preferably processed according to the invention include all plants that have genetic material that confers special advantages, useful characteristic properties to these plants (obtained either by selection and/or biotechnological methods).

Plants and plant varieties, which are also preferably processed according to the invention, are resistant to one or more biotic stress factors, i.e. the specified plants have a preferential protection against animals and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Examples of plants resistant to nematodes are described, for example, in the following patent applications 5: 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12 /192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/294, 912, 12/94, 12/94, 12/791, 192, 192, 192, 192, 192, 192 221.

Plants and plant varieties that can also be processed according to the invention are those plants that are resistant to one or more abiotic stress factors.

Abiotic stress conditions may include, for example, drought, exposure to cold temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogenous nutrients, limited availability of phosphorous nutrients, or avoidance shadows

Plants and plant varieties, which can also be processed according to the invention, are those plants that are characterized by increased yield properties. Increased yield in said plants may result from, for example, improved plant physiology, growth and development, such as water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination efficiency, and accelerated ripening. Also, yield can be affected by improved plant structure (under stressed and non-stressed conditions), including earlier flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and spacing, root growth, seed size, fruit size, pod size , number of pods or cobs, number of seeds per pod or cob, seed weight, increased seed filling, reduced seed dispersal, reduced pod separation and lodging resistance. Further characteristics include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduced anti-nutritional compounds, improved processability and improved storage stability.

Plants that can be treated according to the invention are hybrid plants that already express the characteristics of heterosis, or a hybrid effect that results in overall higher yield, vigor, health and resistance to biotic and abiotic stress factors. Such plants are usually obtained by crossing an inbred parent line with female sterility (female parent for crossbreeding) with another inbred parent line with male sterility (male parent for crossbreeding). Hybrid seeds are usually collected from male-sterile plants and sold to agricultural producers. Plants with male sterility can sometimes be obtained (for example, in cereals) by removing the panicle (that is, by mechanically removing the male reproductive organs or male flowers); however, it is more typical to obtain male sterility as a result of genetic determinants in the plant genome. In this case, and especially if the seeds represent the desired product to be harvested from the hybrid plants, it is typically beneficial to ensure that male fertility in the hybrid plants that contain the genetic determinants responsible for male sterility is fully restored. This can be done by ensuring that the male crossbreeding parents have suitable fertility restoration genes that are capable of restoring male fertility in hybrid plants that contain the genetic determinants responsible for male sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CM5) were, for example, described in Vgazzis species. However, genetic determinants for male sterility may also be located in the nuclear genome. Male sterile plants can also be produced using plant biotechnology techniques such as genetic engineering.

Particularly suitable methods for obtaining male-sterile plants are described in M/O 89/10396, in which, for example, a ribonuclease such as barnase is selectively expressed in tapetum cells in stamens. After that, fertility can be restored by

From the expression in tapetum cells of a ribonuclease inhibitor such as barster.

Plants or plant cultivars (obtained by means of plant biotechnology methods such as genetic engineering) that can be treated according to the invention are herbicide-tolerant plants, that is, the plants have been given tolerance to one or more of the given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation that confers such tolerance to the herbicide.

Plants tolerant to herbicides are, for example, plants tolerant to glyphosate, that is, plants have been given tolerance to the herbicide glyphosate or its salts.

Plants can be made tolerant to glyphosate using a variety of methods.

For example, glyphosate-tolerant plants can be obtained by transforming a plant with a gene encoding the enzyme 33-phosphate synthase (ERBRB5). Examples of such ER5RZ5 genes are the Agoa gene (mutant ST7) of the bacterium ZaItopeiia yurpitigicht (Soppai et al., 1983, Zsiepse 221, 370-371), the SPA gene of the bacterium Adgobasiegisht 5r. (Vagtgu et al., 1992, Cit. Toris5 Riapi Rpuzio!. 7, 139-145), genes encoding ERBR5 petunia (ZPPany et al., 1986, Zsiepse 233, 478-481), ERBRB5 tomato (Sazzeg et al. ., U. Vioiyi. Spet. 263, 4280-4289) or ERZR5 Korakan (MO 01/66704). It can also be a mutated ERBR5. Glyphosate-tolerant plants can also be produced by expressing a gene that encodes the enzyme glyphosate oxidoreductase. Glyphosate-tolerant plants can also be produced by expressing a gene that encodes the enzyme glyphosate acetyltransferase. Plants tolerant to glyphosate can also be obtained by breeding plants containing mutations of the above genes that occur in nature. Plants have been described that express ERBR5 genes that affect tolerance to glyphosate.

Plants that confer tolerance to glyphosate, such as decarboxylase genes, have been described.

Plants tolerant to other herbicides are, for example, plants that have been given tolerance to herbicides that inhibit the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing a herbicide detoxifying enzyme or a mutant glutamine synthase enzyme that is resistant to inhibition. One such effective detoxifying enzyme is the enzyme encoding phosphinothricin acetyltransferase (such as the rod or flap protein from Bo zigerotuse5 species). Plants expressing exogenous phosphinothricin acetyltransferase have been described.

Other herbicide-tolerant plants are also plants that have acquired tolerance to herbicides by inhibiting the enzyme hydroxyphenylpyruvate dioxygenase (HPPD).

Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted into a homogenate. Plants tolerant to HPR inhibitors can be transformed with a gene encoding a naturally occurring resistant HPR enzyme or a gene encoding a mutated or chimeric HPR enzyme as described in UMO 96/38567, UMO 99/24585, MO 99/24586, UMO 2009/144079, UMO 2002/046387 or 05 6,768,044. Tolerance to HPPO inhibitors can also be obtained by transforming the plant with genes encoding certain enzymes that enable the formation of a homogenizer despite the native HPPO enzyme with the help of the HPPO inhibitor. Such plants are described in

UMO 99/34008 and UMO 02/36787. The tolerance of plants to NRPA inhibitors can also be improved by transforming plants with a gene encoding the enzyme prephenate dehydrogenase, in addition to a gene encoding an NRPA-tolerant enzyme, as described in UMO 2004/024928.

Additionally, plants can be made more tolerant to HPRO inhibitors by inserting into their genome a gene that encodes an enzyme that metabolizes or degrades HPRO inhibitors, for example, SUR450 enzymes (see UMO 2007/103567 and UMO 2008/150473).

Other herbicide-resistant plants are plants that have been given tolerance to acetolactate synthase inhibitors (A 5). Known AI5 inhibitors include, for example, sulfonylurea herbicides, imidazolinone, triazolopyrimidines, pyrimidineoxy (thio)benzoates, and/or sulfonylaminocarbonyltriazolinones. Various mutations in the AI5 enzyme (also known as acetohydroxy acid synthase, ANA5) are known to confer tolerance to various herbicides and groups of herbicides, as described, for example, in Tgapei and Umgidpa (Uueya 5siepse 2002, 50, 700-712). The production of plants tolerant to sulfonylurea and plants tolerant to imidazolinone has been described. Other plants tolerant to sulfonylurea and imidazolinone have also been described.

Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, by selection in cell cultures in the presence of the herbicide, or by mutational selection (cf., for example, for soybean O5 5,084,082, for rice

From UMO 97/41218, for sugar beet 05 5,773,702 and MO 99/057965, for lettuce 5 5,198,599 or for sunflower UMO 01/065922).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be processed according to the invention are transgenic plants resistant to an insecticide, i.e. the plants have been given resistance to certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation that confers such resistance to the insecticide.

In the context of the present invention, the term "insecticide-resistant transgenic plant" includes any plant containing at least one transgene containing a coding sequence that encodes: 1) an insecticidal crystal protein from Wasiya5 (hypdiepvi5 or an insecticidal portion thereof, such as insecticidal crystalline proteins prepared by StisKtoge and others (Misgobioiodu apa Moiesshiag

Vioiodu Nemiem5 1998, 62, 807-813), updated by StgisKtoge et al. (2005) in the nomenclature of the toxin

Vasiyi5 "pygipdiepzi5, online at: per:/Lumly. IShevsi.zyb5zeh.as.ik/Note/Meii Stisktoge/VI/), or their insecticidal parts, for example, proteins of Stgu classes of proteins StutABb, StutAs, Stu1B, Stu1C, Stu1o,

StuiE, Stug2AB, StuzAa, or StuzV, or their insecticidal parts (for example, EP-A 1999141 and MUMO 2007/107302), or those proteins encoded by synthetic genes as described in the patent application

OZ 12/249,016; or 2) a crystal protein from Vasiy5 (pygypdiephie or a part thereof) that is insecticidal in the presence of a second crystal protein other than Vasiy5 (pygypdiepsy5 or a part thereof, such as a binary toxin made from Su334 and Su35 crystal protein (Mai. Viotespoi. 2001, 19 , 668-72;

Arriiei Epmigoptus. Misgobio!. 2006, 71, 1765-1774) or a binary toxin consisting of StutlA or StguE proteins and StgutAa or Stgu2AB or Stug2gAe proteins (patent application 05 12/214,022 and

ЕРО8010791.5); or 3) a hybrid insecticidal protein containing parts of two different insecticidal crystal proteins from Wasiya5 (pygipdiepvi5, such as a hybrid of proteins 1) above or a hybrid of proteins 2) above, e.g.

StutA.105 protein obtained with the help of maize event MOMU8034 (MO 2007/027777); or 4) the protein of any one of items 1) - 3) above, where some, preferably from 1 to 10, amino acids have been replaced by another amino acid, obtaining a higher insecticidal activity against the target insect species, and/or expanding the range of affected targets insect species, and/or as a result of changes in the coding DNA in the process of cloning or transformation, such as the SguZzB1 protein in the maize events MOM863 or MOM88017, or the SguzA protein in the maize event MIKBO4; or 5) an insecticidal secreted protein from Vasiya5 IPyhipdiepoiz or Vasi segei5, or its insecticidal part, such as vegetative insecticidal proteins (MIR), listed in: pEr://mmly evsi.iv5zeh.as.ik/Ноте/Мейй Стисктоге/Ви/ mir.piti, for example, proteins from the class of proteins

MIRZAa; or b) a secreted protein from Wasiya5 Ixyhipdiepsis or Wasiya5 segei5 that is insecticidal in the presence of a second secreted protein from Wasiya5 IpPyhipdiepvi5 or B. segets5, such as a binary toxin derived from the MIRTA and MIR2A proteins (MO 94/21795); or 7) a hybrid insecticidal protein containing parts from different secreted proteins from Wasiya5

Iihipdiepvi5 or Vasiyi5 segets5, such as a hybrid of proteins in 1) above or a hybrid of proteins in 2) above; or 8) the protein of any one of items 5) - 7) above, where some, preferably from 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity against target insect species, and/or to expand the range of affected targets insect species, and/or as a result of changes induced in the coding DNA by cloning or transformation (while still encoding an insecticidal protein), such as the MIRZAa protein in the cotton WTO 102 event; or 9) a secreted protein from Wasiya5 "pygypdieppoie or Wasiya5 segei5, which is insecticidal in the presence of a crystalline protein from Wasiya5 (Pygpdiepvi5, such as a binary toxin derived from the proteins MIZ and StutA or StguiE (05 patent applications 61/126083 and 61/195019), or a binary toxin derived from the protein MIZ and Stu2Aa or Sgug2AbB or Sgug2Ae proteins (patent application 12/214,022 and

ER 08010791.5); or 10) a protein according to item 9) above, where some, preferably from 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity against the target insect species, and/or to expand the range of affected target insect species, and/or in as a result of changes induced in the coding DNA as a result of cloning or transformation (while still encoding the insecticidal protein).

Apparently, transgenic plants resistant to insecticides as used herein

The invention includes any plant containing a combination of genes encoding proteins of any of the above classes 1-10. In one embodiment, the insecticide-resistant plant contains more than one transgene encoding a protein of any of the above classes 1-10, expanding the range of affected target insect species or delaying the development of insect resistance in the plant by using different proteins, the insecticide to the same insect target species but with a different mode of action, eg binding to other receptor binding sites in the insect.

In the context of the present invention, "insecticide-resistant transgenic plant" further includes any plant containing at least one transgene containing a sequence for producing a double-stranded RNA that, upon consumption by an insect pest, prevents the growth of that pest.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation that provides such resistance to stress. Particularly preferred stress-tolerant plants include the following: a. plants that contain a transgene capable of reducing the expression and/or activity of the poly(Adr-ribose) polymerase (RAPCR) gene in plant cells or plants; r. plants that contain a transgene that enhances tolerance to stress, capable of reducing the expression and/or activity of genes encoding RAKO, plants or plant cells; with. plants that contain a stress tolerance-enhancing transgene encoding a functional plant enzyme of the nicotinamide adenine dinucleotide utilization biosynthetic pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthesis, or nicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by means of plant biotechnology methods such as genetic engineering) which may also be processed according to the invention exhibit altered quantity, quality and/or storage stability of the harvested product and/or altered properties of specific ingredients of the harvested product, such as: 1) Transgenic plants that synthesize modified starch, which is altered with respect to its chemophysical properties, especially amylose content or amylose/amylopectin ratio, degree of branching, average chain length, distribution of side chains, viscosity character, gel resistance, size grains and/or starch grain morphology compared to synthetic starch in plant cells or wild-type plants, such that this modified starch is more suitable for certain applications. 2) Transgenic plants that synthesize non-starch carbohydrate polymers or that synthesize non-starch carbohydrate polymers with altered properties compared to wild-type plants without genetic modification. Examples are plants that produce polyfructose, especially of the inulin and levan type, plants that produce alpha-1, 4-glucans, plants that produce alpha-1, b6-branched alpha-1, 4-glucans, and plants that produce alternan 3) Transgenic plants that produce hyaluronate. 4) Transgenic plants or hybrid plants, such as onions, with special properties such as "high soluble solids", "low burning" (I P) and/or "long storage" (I. 5).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be processed according to the invention are plants such as cotton with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation that gives such changed fiber characteristics, and include: a) plants, such as cotton, containing an altered form of cellulose synthase genes; p) plants, such as cotton, which contain an altered form of heme/2 or heme/3 homologues of nucleic acids, such as cotton with increased expression of sucrose phosphate synthase; c) plants, such as cotton, with increased expression of sucrose synthase; a) plants, such as cotton, in which the regulation of the opening time of the plasmodesmal channel on the basis of fiber cells has been changed, for example, by down-regulation of fiber-selective B-1, З-glucanase; f) plants, such as cotton, that have fibers with altered reactivity, for example, by expression of the M-Acetylglucosaminetransferase gene, including poas, and chitin synthase genes.

Plants or plant varieties (obtained by means of plant biotechnology methods, such as genetic engineering) that can also be processed according to the invention are plants, such as oilseed rape plants or the Vgazv5isa family, with altered characteristics of the oil structure. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation that confers such altered characteristics of the oil, and include: a) plants, such as rapeseed plants, which produce an oil having a high oleic acid content;

B) plants, such as oilseed rape plants, which produce oil with a low linolenic acid content; c) plants, such as rapeseed plants, which produce oil that has a low level of saturated fatty acids.

Plants or plant cultivars (which may be obtained by means of plant biotechnology methods such as genetic engineering) which may also be processed according to the invention are plants such as potatoes which are resistant to viruses, for example the U virus of potato ( 5230 and 5233 events from Tesporiapi, Agdepiip), or which are resistant to diseases such as potato late blight (for example, the KV gene), or which show reduced cold-induced sweetness (carrying the MI-Ipy, II-IMM genes) or which show dwarfism phenotype (A-20 oxidase gene).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be processed according to the invention are plants, such as oilseed rape or Vgazv5isa family plants, with altered seed destruction characteristics. Such plants may be obtained by genetic transformation, or by selection of plants containing a mutation conferring such altered characteristics, and include plants such as oilseed rape with delayed or reduced seed destruction.

Particularly suitable transgenic plants that can be treated in accordance with the invention are plants with transformation events or combinations of transformation events that are the subject of issued or pending applications for non-regulated status in the United States with the Health Inspection Service I Animal and Plant Science (ARNIB) of the United States Department of Agriculture (SHBOA). Information on this is available at any time from ARNIZ (4700 Kimeg Koai Kimegdaiye, MO 20737, О5А), for example, through the website pErulmmilmy.arpiz.izaa.dom/рг5/пой гед.пити. as of the date of submission of this application, petitions with the following information have either been issued or are pending consideration at ARNIB:

I) Petition: identification number of the petition. A technical description of the transformational event can be found in a specific solicitation document available from ARNIS on the website under solicitation number. These pleadings are therefore incorporated by reference. - Extension of the request: Reference to an earlier request for which an extension of the scope or term is requested. - Institute: Name of the person presenting the request. - Regulated materials: Specified plant species. - Transgenic phenotype: A characteristic given to a plant by a transformation event. - Transformational event or line: Name of phenomenon(s) (sometimes also referred to as line (Y)) for which unregulated status is claimed. - ARNIZ5 documents: Various documents that have been published by ARNIZ regarding the request or which can be obtained from ARNIZ upon request.

Particularly suitable transgenic plants that can be processed according to the invention are plants that contain one or more genes that encode one or more toxins and are transgenic plants available under the following trade names:

MESKO SAKOF (e.g. maize, cotton, soybeans), KposKoike (e.g. maize),

Viedagaya (e.g. maize), Vi-higtaya (e.g. maize), 5iahipkF (e.g. maize), VoiYidagaF (cotton), MysoipF (cotton), Mysoip Z33VF (cotton), MaishgedagaF (e.g. maize), RgoiesiafF and Meul/ eake (potatoes). Examples of herbicide-tolerant plants that must be listed are cereal varieties, cotton varieties, and soybean varieties that are available under the following trade names: Coipair KeaduFf (glyphosate tolerant, e.g. corn, cotton, soybeans), Irepu I ipkF ( tolerant to phosphinothricin, such as oilseed rape), IMIE (tolerant to imidazolinone) and 5C5FO (tolerant to sulfonylurea), such as corn. Herbicide-resistant plants (plants that have been conventionally bred for tolerance to the herbicide) that must be listed include varieties sold under the name SeagiedF (eg, corn).

Particularly preferred transgenic plants that can be processed according to the invention are plants that contain transformation events, or a combination of transformation events, and which are listed, for example, in a database for various national or regional government regulatory bodies (see, for example . 5!Crtius).

Active compounds or compositions according to the invention can also be used to protect materials, to protect industrial materials from attack and destruction by undesirable microorganisms, for example, fungi and insects.

Additionally, the combinations according to the invention can be used as antifouling compositions, alone or in combination with other active compounds.

Industrial materials in the context of this invention refer to inanimate materials that have been manufactured for use in industry. For example, industrial materials that are intended to be protected by active compounds according to the invention from microbial alteration or destruction may be adhesives, containers, paper, wallpaper, and board, textiles, carpets, leather, wood, paints, and plastics. cooled lubricants and other materials that can be infected or destroyed by microorganisms. Parts of production facilities and buildings, such as water cooling systems, cooling and heating systems and ventilation and air conditioning units, which may be damaged by the proliferation of microorganisms, may also be mentioned in the context of materials to be protected. Industrial materials within the scope of this invention preferably include adhesives, containers, paper and cardboard, leather, wood, paints, refrigerated lubricants and heat transfer fluids, especially preferably wood. Active compounds or compositions according to the invention can prevent side effects such as rotting, destruction, discoloration, discoloration or mold formation. In addition, the compounds according to the invention can be used to protect objects in contact with sea or salt water, especially hulls, screens, nets, structures, moorings and signaling systems, from decay.

The method according to the invention for controlling unwanted fungi can also be used to protect stored goods. In this invention, stored products 60 denote natural substances of plant or animal origin or their processed products of natural origin, for which protection is desired for a long time.

Commodities of plant origin, such as for example plants or parts of plants such as stems, leaves, tubers, seeds, fruits, grains, may be protected fresh or after processing by (pre)drying, moistening, grinding, threshing, pressing or roasting Commodities also include timber, either unprocessed such as construction timber, electric poles and batteries, or in the form of finished products such as furniture. Commodities of animal origin are, for example, leather, skin, fur and hair. Active compounds according to the invention can prevent undesirable effects such as rotting, decomposition, discoloration, discoloration or mold formation.

Some pathogens of fungal diseases that can be treated according to the invention may be mentioned by way of example, but in no way limited:

Diseases caused by pathogens of true powdery mildew, such as, for example, Vishtegia species, such as, for example, Vishtegia dgatipie; Rhodozrpayega species, such as, for example, Rhodozrpayega Ieisoihispa; species of 5rpaegoipesa, such as, for example, ZrpaegoiShyesa

Thyidipea; species of Opsiptsia, such as, for example, Opsipsha pesaiog; diseases caused by pathogens of rust diseases, such as, for example, species

Nepiieiia, such as, for example, Netiivia maziaigih; species of Rpakorzoga, such as, for example, Rpakorzhoga raspugpigi and Rpakorzoga teiirotiae; species of Rissipia, such as, for example, Rissipia hesopaia or

Rissipia igyisipa; types of Ogotusev, such as, for example, Ogotusev arrepaisciativ5; diseases that are caused by pathogens from the Ootuseii group, such as, for example, spp

Vgetia, such as, for example, Vgetia Iasiisaye; species of Regopozroga, such as, for example, Regopozroga ribi or R. Bgazzisae; types of RPpuiorpiyoga, such as, for example, RPpuioripoga iptebiap5; species

Riaztoraga, such as, for example, Riazitoraga myisioia; types of Rzheydoregopozrog, such as, for example,

Rzeidoregopozroga pitiyai or Rzhepdoregopozroga sibepvib; species of Ruipisht, such as, for example,

Ruipisht iyitit; leaf spot disease and leaf wilt disease caused by, for example, the following species: AKegpagia species, such as, for example, AKegpagia 50Iapi; species of Segsozroga, such as, for example, Segsozroga reiissoia; species of Siadiozrogyst, such as, for example, SiIadiozrogyit sisytegipit; species of Sospiioroisn5, such as, for example, SospiioBboii5 5aiimiv (sopidia togt: Ogespviega, 5up: NeItipipozrogisht); types of SoPPefoihispit, such as, for example, SoPeshuigispit Iipateivapiit; species of Susiosopisht, such as, for example, Susiosopicht oiIeadipit; species of Oiarogie, such as, for example,

Oiarogpye siigi; types of Eilipoe, such as, for example, EiliIi5ipoe Tam/seitsi; species of Clioeozorogist, such as, for example, Cioeozorogist IaeiiisoYog; types of SiotegeiPa, such as, for example, SiotegeiPa sipdashatsa; types of syidpagaiya, such as, for example, scidpagaiya rijeiya; types of I eriozrpaegia, such as, for example,

IHeriozrpaeegtia tasciap5; species of Madparogiye, such as, for example, Madparogiye dgyzea; species

Misgodospicht, such as, for example, Misgodospicht pimaIe; Musozrpaigeia species, such as, for example,

Musozrpayegeiia dgatipisoia and M. Yaiepviz; species of Rpaeozrpaegia, such as, for example, Rpaeozrpaegia podogyt; species of Rugeporpoga, such as, for example, Rugeporpoga iege5; Cathygia species, such as, for example, Cathygia soPo-sudpi; types of Kpupspozrogitst, such as, for example, Kpupspozrogitt zesaiib; types of zeryogia, such as, for example, zeryogia aria; species of Turpsia, such as, for example, Turpsia ipsaptaya; species of Mapingia, such as, for example, Mapishgia ipaedvacii5; diseases of roots and stems caused, for example, by Sogpisisht species, such as, for example, Sogpisisht dgatipagit; by ERyzagyit species, such as, for example, Ryzagisht ohuzrogyt; by Saeshtappotuse5 species, such as, for example, Saeshtappotuse5 dgatipie; species

KPpi2osiopia, such as, for example, Kpi2osiopia 50Iapi; by species of Tarevsia, such as, for example,

Taresia Asyshogti; species of TPiveiamiorzi5, such as, for example, TPiveiamiorzi5 Bavzisoia; diseases of cobs and tassels (including corn cob shafts) caused, for example, by AKegpagia species, such as, for example, Ayegpagia 5rr.; by types of Azregoyiv5, such as, for example, Azregoyy5 Pama5; species of Siadozroghist, such as, for example, Siadozrogiit siadozrogioide5; by Siamiser5 species, such as, for example, Siamiser5 rygrigea; by ERizagisht species, such as, for example, Ryzagisht syitogyt; types of syrregeIPa, such as, for example, sZirregePa 7eae; by species of Mopodharpegia, such as, for example, Mopodharpeia pimaiie; by species of Zeriogia, such as, for example, Zeriogia podogyta; diseases caused by powdery mildew, such as species

Zrpaseipoipesa, such as, for example, Zrpaseioipesa heiapa; species of TiPeia, such as, for example, TSheia sagpie5, T. sopygomegza; species of Ogosuziya5, such as, for example, Ogosubiiz ossina; types of O5iyado, such as, for example, O5zShado pida, 0. pida igysi; 60 fruit rots caused, for example, by species of Azregadiyn5, such as, for example,

AzregoiPi5 Pamib5; Voiguiis species, such as, for example, Voiguiis sipegea; species of Repisiysht, such as, for example, Repisiysht echrapsite and R. rygrigodepit; by Zsiegoiipia species, such as, for example, Zsiegoiipia zsiegoyogit; types of Mepisiisht, such as, for example, Mepisiisht aIroaigit; rotting and vascular diseases transmitted through seeds and soil, and also seedling diseases caused, for example, by species of Eizagisht, for example, ERizagiyt siitogyt; species of Rpuiorpipoga, for example, Rpuiorpiyoga sasiogit; Ruijpisht species, for example

RuiSisht and Shchitit; by KpPi2osiopia species, for example, KPi2osiopia zooiapih by Zsiegoiit species, for example, Zsiegoiit goii5ii; cankers, galls and witches' brooms caused, for example, by Mesigia species such as, for example, Mesigia daPdepa; vascular diseases caused, for example, by Mopiiipia species, such as, for example, Mopiiipia Iaha; deformations of leaves, flowers and fruits caused, for example, by species of Tharphip, e.g.

Tarnpipe deptapv; degenerative diseases of woody plants caused, for example, by species of Evsa, for example, RPaeotopiePa spiatudozoroga and RPaeoasgetopisht aeorpisht and Eotiirogia theaiiietapvea; flower and seed diseases caused by, for example, Voiguii species, e.g.

Voiguii5 sipegeea; diseases of plant tubers caused, for example, by KpPi2osiopia species, such as, for example, KpPi2osiopia 5oiapi; by types of NeiYitipipozrogisht, such as, for example, NeiItipipo5rogiit zoiYapi; diseases caused by bacterial pathogens, such as species

Hapipotopav, for example, Hapipotopah satrevzigiz ru. speaks out; species of Rzhendotopavz, for example

Rzepydotopaz zugipday ru. Iaspgutape; by Egmipia species, for example, Egmipia atuomoga.

The following soybean diseases can mainly be controlled:

Fungicidal diseases on leaves, trunks, pods and seeds caused by the following pathogens, for example, leaf spot caused by AKcegpagia (APegpagia 5res.

Zo aiigap5 iepiizzita), Apipygaspose (SoPefoiihispyt dioeozrogoide5 detatsyitst mag. igypsaysht), brown spot (zZeriogia diusipe5), spotting and damage to leaves caused by cercospora (Segsozroga Kikispii), damage to leaves caused by spoaperpoga (Spoaperpoga iptyparoriga (Zupega M.) , leaf spot caused by dasishiornoga (Oasishiorpoga diusipe5), irregular powdery mildew (Regopozroga tapz5Ppygisa), leaf damage caused by agespziega (Ogespziega diusipe), ring leaf spot (Segsozroga 5o)|ipa), leaf spot caused by Ieriozrpaegyiypa (Heriozrpagegiyypa igioiiyi), leaf spot caused by rpuiobiisia (RPpuiobviisia 5oiaesoia), damage to pods and stems (Rpotorzhiv 5oiiae), true powdery mildew (Misgozrpayega aiivza), leaf spot caused by rugepospaeia (Rugepospaeia diusipe5), aerial rhizoctonia, foliar, and web damage (KpPig2hosiopia 5oYapi), rust (RpaKorzoga raspugpigi, Rpakorzoga te yrotiae), scab (Zrpaserta diusipe5), leaf spotting caused by v5ietrpuiint (5etrpPpuiit roiguosit), target-like spotting (Sogupezroga savzviisoia).

Fungicidal diseases of roots and leaves caused by such pathogens as, for example, black root rot (SaYopesigia sgoiaiagiae), ash rot (Mashorpotypa rpazeoiipa), fusarium spot or wilt, root rot, and pod and branch rot (Bizagist ohuzrogyt, Eizagist ogiposega5 , Ryzagisht 5etyessht,

Eizagisht ediizeii), root rot caused by tusoiIeriodissis (MusoiIeriodivsiv Iegtevigiv), peoso5ito5zroga (Meosoz5itozroga mahip'esia), wilting of pods and stems (Oiarogye rpaseoiYogit), stem ulcers (Oiarogye rpaseioigit mag. sations), rot caused by teregotayurnogai (Rdapuz ), brown stem rot (RPiaiirpoga dgedaia), fungal rot (Rushtiit arpapideptasht, Ruiyisht itedshage, Rushtisht debaguapyt, Ruiyisht tugioiuisht, Rushisht iKitit), root rot, stem decay and waterlogging caused by rhizoctonia (EPi2osiopia 5oYapi), stem decay caused by sclerotinia ( 5siegoiipia 5siIegoiogit), southern sclerotial rot (Zsiegoiipia goiibbi), root rot caused by Piveiamiorvs (Tpieiamiorvziv Bavisoia).

Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime-forming organisms. Active compounds according to the invention mainly act on fungi, especially wood-discoloring and wood-decomposing fungi (Vazidiotuseii), and on slime-forming organisms and algae. Examples include microorganisms of the following genera: AcKegpagia, such as AKegpagia

Iiepii5; Avregoy5, such as AvzregoyShy5 fit; Spaeitisht, such as Spaeitisht adiorosite;

Sopiorpoga, such as Sopiorpoga rieiapa; IHepiipib5, such as Hepiipi5 (dhipi5; RepishshShiit, such as

Repisiyit diaisit; Roiurogy5, such as Roiurogy5 megvisoiog; Aigeobavzidiitis, such as Angeobavzidiitis ryishape; Zsiegorpota, such as Zsiegorpota riuorpiia; Thispodegta, such as Thispodegta migiae;

E5cPegispia, such as E5cPpegispia soybean; Rzepdotopah, such as Rzespdotopa5 aegidiposa; ziarpuiosossiv, such as Ziarpuiosossiv ashigeiv5.

Additionally, the active compounds according to the invention also have very good antifungal activity. They have a very broad spectrum of antifungal activity, especially against dermatophytes and yeasts, molds and biphasic fungi (for example, against Sapaida species such as Sapaida aiirisap5, Sapaida diabgaga), and Eridepporpuiop Possozuit, species

AzregoiNPy5, such as AvreguyShiv5 pideg and Avregodyi5 Titidayi5, species of Tgisporpuiop, such as

Typsporpuiop tepiadhorpuyez, species of Mysgozrogop, such as Mysgozrogop sapi and Aidopcipia. The list of these fungi should not be considered as a limitation of the covered fungal spectrum, and is purely illustrative in nature.

Thus, the active compounds according to the invention can be used for both medical and non-medical indications.

When using the active compounds according to the invention as fungicides, application rates can vary in a relatively wide range, depending on the type of application. The rates of introduction of active compounds according to the invention are - in the case of processing plant parts, for example, leaves: from 0.1 to 10,000 g/hectare, preferably from 10 to 1000 g/hectare, more preferably from 50 to 300 g/hectare (in in the case of application by wetting or percolation, it is even possible to reduce application rates, especially if inert substrates such as mineral felt or perlite are used); - in the case of seed treatment: from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12 .5 g per 100 kg of seeds; - in case of tillage: from 0.1 to 10,000 g/hectare, preferably from 1 to 5,000 g/hectare.

These application rates are given only as an example and do not limit the scope of the invention.

Active compounds or compositions according to the invention, in this way can

To be used to protect plants for a certain period of time after treatment against the attack of the indicated pathogens. The period during which protection is provided generally lasts from 1 to 28 days, preferably from 1 to 14 days, especially preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of plants with active compounds, or up to 200 days after seed processing.

Additionally, by processing according to the invention, it appears possible to reduce the mycotoxin content in the collected material and in food products and feed products prepared from them. Especially, but not exclusively, the following mycotoxins can be mentioned in this case: deoxynivalenol (SOM), nivalenol, 15-Ac-dop, Z-Ac-aop, Ta- and HT 2-toxin, fumonisins, zearalenone, moniliformin, fusarin, diacetoxyscirpenol (BAB), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, horn alkaloids and aflatoxins obtained, for example, with the help of the following mushrooms: Ryzagiyt 5res., such as, in particular, Ryzagiyt asitipaisht, E. amepasesht, E. sgooKu" emPepze, RE. sitogyt, E. dgaminagyte (ZirbegeiPa 7eaye), E. ediizeii, R. tiiKogoi, GE. tivagit, R. okhuvrogyte, RE. rgoiiiTegaiiit, ER. roae, RE. rzepdodgaminagyte, R. vatrisipit, R. vysikri, E. zetiesiit, R. 5oiapi, E. 5rogoihispoiYidev, E. Iapdzeipiae, R. zybdishipapv, GE.

If appropriate, the compounds of the invention may, at certain concentrations or application rates, also be used as herbicides, antidotes, growth regulators or plant improvers, or as microbicide, for example as fungicides, antifungals, bactericides, viricides (including means against viroids) or as means against MG O (mycoplasma-like organisms) and CI O (rickettsia-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

The active compounds according to the invention intervene in plant metabolism and therefore can also be used as growth regulators.

Plant growth regulators can have different effects on plants. The effect of the compounds depends mainly on the time of application based on the stage of plant development and also on the amounts of the active compound applied to the plants or their environment and on the type of application. In each case, growth regulators must have a certain desired effect on the crops.

Compounds that regulate plant growth can be used, for example, to inhibit vegetative growth of plants. Such growth inhibition is of economic interest, for example in the case of grasses, as it makes it possible to reduce the frequency of grass mowing in ornamental gardens, parks and sports facilities, roadsides, airports or fruit crops. It is also important to inhibit the growth of herbaceous and woody plants on roadsides and near pipelines or overhead cables or in general in areas where strong plant growth is undesirable.

The use of growth regulators to inhibit the longitudinal growth of grain crops is also important. Thus, it is possible to reduce or completely eliminate the risk of plants lying down before harvesting. In addition, in cereal crops, growth regulators can strengthen the stem, which also acts against lodging. The use of growth regulators to stabilize and strengthen the stems allows you to use higher rates of fertilizer application to increase yield without any risk of grain crop lodging.

In many crops, the inhibition of vegetative growth allows for more compact planting, and thus allows for higher yields on the soil surface. Another advantage of the shorter plants produced in this way is that the crop is easier to cultivate and harvest.

Inhibition of the vegetative growth of the plant can also lead to an increase in yield in such a way that nutrients and assimilates show more advantages for flowering and fruit formation compared to the vegetative parts of the plant.

Often, growth regulators are also used to stimulate vegetative growth. This is a huge advantage when collecting vegetative parts of plants. However, stimulation of vegetative growth can simultaneously also promote generative growth, thus producing more assimilates, leading to more or larger fruits.

In some cases, increased yield can be achieved by influencing plant metabolism without any detectable changes in vegetative growth. In addition, growth regulators can be used to change the composition of plants, which in turn can lead to improved quality of harvested products. Thus, it is possible, for example, to increase the sugar content in sugar beet, sugar cane, pineapples, as well as in citrus fruits

From fruits, or to increase the protein content in soybeans or in grain crops. It is also possible, for example, to inhibit, by means of growth regulators, the breakdown of desired components, such as, for example, sugar in sugar beet or sugar cane, before or after harvest. In addition, there may be a positive effect on the production or elimination of secondary plant ingredients. As an example that can be mentioned, it is possible to indicate the stimulation of the flow of latex in rubber trees.

Under the influence of growth regulators, parthenocarpic fruits can be formed. In addition, it seems possible to influence the sex of flowers. It is also possible to obtain sterile pollen, which is extremely important in the selection and production of hybrid seeds.

By using growth regulators, you can control the branching of plants.

On the one hand, by destroying the dominance of the top, it seems possible to promote the growth of lateral shoots, which can be extremely desirable especially in the cultivation of ornamental plants also in combination with growth inhibition. However, on the other hand, it also seems possible to inhibit the growth of side shoots. This effect is of particular interest, for example, when cultivating tobacco or cultivating tomatoes.

Under the influence of growth regulators, the number of leaves on plants can be controlled in such a way that plants are defoliated at the desired time. Such defoliation is extremely important in the mechanical harvesting of cotton, but is also of interest for the harvesting of other agricultural crops, such as, for example, in viticulture.

Defoliation of plants can also be done to reduce transpiration of plants before transplanting them.

Growth regulators can also be used to control fruit cracking. On the one hand, it seems possible to prevent the cracking of unripe fruits. On the other hand, it is also possible to promote fruit cracking or even stop flowering to achieve the desired mass ("thinning") to break the rotation. Alternation is understood as a characteristic of some fruit species for delivery, with the help of endogenous factors, which strongly change harvests in different years. In conclusion, by using growth regulators during harvest, it appears possible to reduce the force required to detach the fruit to enable mechanical harvesting or to facilitate manual harvesting. 60 Growth regulators can also be used to achieve faster or even delayed maturation of harvested material before or after harvest. This is a huge advantage, as it provides optimal adaptability to market demands. In addition, in some cases, growth regulators can affect the coloring of fruits.

In addition, growth regulators can also be used to achieve ripening concentrated in a certain period of time. This makes it possible to harvest mechanically or manually in one operation, for example in the case of tobacco, tomatoes or coffee.

Through the use of growth regulators, it is also possible to influence the dormancy of seeds or buds of plants, so that plants such as, for example, pineapples or ornamental plants in nurseries germinate, produce shoots or flower during a period of time in which they normally cannot to do it In areas where there is a risk of frost, it may be desirable to delay seed budding or germination with growth regulators to avoid late frost damage.

In conclusion, growth regulators can induce plant resistance to frost, drought, or high soil salinity. This makes it possible to cultivate plants in areas that are normally unsuitable for this.

The listed plants can be treated according to the invention in an extremely favorable way with the help of compounds of the general formula (I) and/or compositions according to the invention.

The preferred ranges indicated above for the active compounds or compositions also apply to the treatment of these plants. Special attention is paid to the treatment of plants using compounds or compositions specifically indicated in the text of this application.

The invention is illustrated by the examples below: However, the invention is not limited to the examples.

Examples of receipt

Preparation of the Mo Z compound (method A)

Ne nH is no sn» vv | M "- in 2

E Z M

To 0.70 g (3.3 mmol) of 4-Ctrifluoromethyl)sulfanylbenzenethiol, dissolved in 20 ml of M, M-dimethylformamide, 0.13 g (60 95, 3.3 mmol) of sodium hydride was added at room temperature in an argon atmosphere , and the reaction mixture was stirred at room temperature for 1

From an hour. After that, 0.5 g (3.0 mmol) of 5-(2-isopropyloxiran-2-yl)pyrimidine was added, and the reaction mixture was stirred at 100C for 12 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and a saturated aqueous solution of sodium chloride and ethyl acetate were added to the residue. The organic phase was separated, dried over sodium sulfate, filtered and concentrated. The crude product was then purified by column chromatography (1:11 cyclohexane/ethyl acetate) to afford 0.11 g (10 95) of the desired product.

Preparation of 5-(2-isopropyloxiran-2-yl)pyrimidine o g) what.

In an argon atmosphere, 50 ml of dimethyl sulfoxide was slowly added dropwise to 8.06 g (37 mmol) of trimethylsulfoxonium iodide and 1.47 g of sodium hydride (60 95.37 mmol). After that, the reaction mixture was stirred at room temperature for 15 minutes, and 5.00 g (33 mmol) of 2-methyl-1-(5-pyrimidinyl)-1-propanone, dissolved in 10 ml of tetrahydrofuran, was added.

The reaction mixture was stirred at 50 "C for 90 minutes. After that, the reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium chloride and ethyl acetate were added to the residue. The organic phase was separated, dried over sodium sulfate, filtered and concentrated. This provided 1 .36 g (25 95) of the desired product, which was reacted without further purification.

Obtaining the compound Mo 12 (method B)

NUE sn, shchi) sn" (c)

ZO

-

E c) M

In an argon atmosphere, a mixture of 3.8 g (13.6 mmol) of 3,3-dimethyl-1-(4-trifluoromethoxy)phenoxy butan-2-one and 2.50 g (15.6 mmol) of 5-bromopyrimidine in a mixture of 20 ml of anhydrous tetrahydrofuran and 20 ml of anhydrous diethyl ether was cooled to -120 °C. After that, n-butyllithium (6.55 ml, 2.5 M, 16.3 mmol) was added slowly with stirring. After the addition was complete, the reaction mixture slowly warmed to room temperature overnight. 100 mL of 10 95 ammonium chloride solution was added to the reaction mixture, and the organic phase was separated. The organic phase was then washed with 1N hydrochloric acid and saturated aqueous sodium chloride, dried over sodium sulfate, and filtered , and the filtrate was concentrated. The crude product was then purified by column chromatography (1:11 cyclohexane/ethyl acetate) to afford 1.46 g (30 95) of the desired product.

Preparation of compound Mo 9 (method C)

BUT sn, (c) not sn, ru

E c) M

Up to 0.33 g (1.0 mmol) of 2-methyl-1-(pyrimidin-5-yl)-2-I(4-trifluoromethoxy)phenoxy)| of propan-1-one dissolved in 10 ml of toluene, 1.0 ml (3.0 M solution in diethyl ether, 3.0 mmol) of methylmagnesium bromide was added at -78 "C in an argon atmosphere, and the reaction mixture was stirred at -78 "C for 30 minutes. The reaction mixture was mixed with 100 ml of a saturated aqueous solution of ammonium chloride and 100 ml of toluene, and the organic phase was separated. The organic phase was dried over sodium sulfate, filtered and concentrated. After that, the crude product was purified using column chromatography. This provided 0.12 g (36 95) of the desired product.

Compounds 9, -11, 13-16 and 22-27 were obtained in a similar way.

Preparation of 2-methyl-1-(pyrimidin-5-yl)-2-(4-(trifluoromethoxy)phenoxy)propan-1-one

E|c) M

Coo)

A mixture of 4.4 g (25.0 mmol) of 4-trifluoromethoxyphenol and 15.5 g (112.5 mmol) of potassium carbonate in 37.5 ml of anhydrous dimethyl sulfoxide was stirred at room temperature for 2 hours. After that, the reaction mixture was heated to 60 "C, and 25.7 g (112.5 mmol) of 2-methyl-1-(pyrimidin-5-yl)propan-1-one dissolved in 12.5 ml of dimethyl sulfoxide was added. After the addition was complete, the reaction mixture was stirred overnight. The reaction mixture was poured into 250 mL of water and extracted with 250 mL of ethyl acetate. The organic phase was separated and then washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated. The crude product was then purified by column chromatography to afford 1.24 g (14 95) of the desired product.

Preparation of 2-bromo-2-methyl-1-(pyrimidin-5-yl)propan-1-one by es

Shchi not sleep, ru

WITH

At room temperature, 11.8 ml (229.8 mmol) of bromine dissolved in 111.5 ml of hydrobromic acid was added to 28.7 g (191.5 mmol) of 2-methyl-1-(pyrimidin-5-yl) of propan-1-one, dissolved in 463 ml of hydrobromic acid. After the addition was complete, the reaction mixture was stirred overnight. After that, the reaction mixture was concentrated under reduced pressure. This provided 50.8 g (91 95) of the desired product, which was reacted without further purification.

Preparation of 3,3-dimethyl-1-I4-(trifluoromethoxy)phenoxy). butan-2-one (method E) about about

YES

E about

With stirring and at room temperature, a solution of 5.5 g (31 mmol) of bromo-3,2-one in 50 ml of acetonitrile was slowly added dropwise to a mixture of 5.5 g (31 mmol) of 4-trifluoromethoxyphenol and 4.27 g ( 31 mmol) of potassium carbonate in 100 ml of acetonitrile. After the addition was complete, the reaction mixture was stirred at reflux temperature overnight.

The solid was filtered off and the filtrate was concentrated. The residue was resuspended in 50 ml of ethyl acetate and the organic phase was washed with ice-cold 1M aqueous sodium hydroxide solution and water. The organic phase was separated, dried over sodium sulfate, filtered and concentrated. After that, the crude product was purified using column chromatography. This provided 2.22 g (26 95) of the desired product.

Table 1 v'v" - 4 v U v v v! x E vv

Ge 7

Ma, M --y (I) m/min in |v. in |-SeV'|vVn|vn|vV| 4 credits Physical education //-:-

Tony me | nn education "(Z 2 109|Nni ik | no | n | 2osv | Nini NnNI 00001030 4-5SEz IooR 3.28 Ii, (MANI -375 "NMR (400 MHz, DMSO-av): b - 0, 93 (5, 9H), 3.56 (a, 9-12

Gu, 1H), 4.12 (a, 9-12 Hz, 1H), 4 Z N IVy H Nn 4-5SEz Н Н H 15.56 (5, 1H), 7.44 (a, 9-8 Hz , 2H), 7.58 (y, 9-8 Hz, 2H), 8.82 (5, 2H), 9.04 (5, 1H) freq. per million

Ion Me | nn | A5se» IooR 2.56 14, (MANI -358 "NMR (400 MHz, DMSO- av): b - 0.90-0.99 (t, 1Н), 1.04- 2, 3- 1, 10 (t, 1H), 1.32-1.45 (t,

N | difluoro-Hn Hn 4-OSEz |-СНаСНо| НОО2Н), 6.47-6.51 (t, ЗН), 6.92- phenyl 7.02 (t, ЗН), 7.22 (9, 1Н), 8.09 (а9, 1Н), 8, 77 (in, 2H); 9.06 (5.1H) frequent. per million

Zo

Table 1 inV' in? And in the--

St. in the day. t

Ma M ke () me| ХА in |in |in |-SevВ| in vVe| In | o Physical data/- "H-NMR (400 MHz, DMSO-abv): b - 0.89 (5, 9H), 2.09-2.21 (t, 2H), 2.52 (aa, 1n), 2.65 7 Сн Нн IVy Н Н 4-50Ez Н Н nava, tn), 3.32 (rev, 1Н), 7.32 (а, 2Н), 7.60 (а, 2Н), 8.83 ( 5, 2H), 9.03 (5, 1H) parts per million "H-NMR (400 MHz, DMSO- av): b - 1.01-1.16 (t, 2H), 1.36- 2, A- 1.49 (t, 2H), 6.55-6.59 (t,

N | difluoro-НН 4-5СЕз |-СНаСНо-| NN |ZN), 6.88 (19, 1H), 7.22 (Id, phenyl 1H), 7.32 (a, 2H), 8.08 (aa, 1H), 8.77 (c, 2H) ; 9.04 (5.1H) frequent. per million "H-NMR (400 MHz, DMSO-abv): b - 1.01 (5, ZN), 1.33 (5, ZN), and 1.70 (5, ZN), 5.76 ( 5, 1H), 6.99 9 N Me H H 4-OSEz | Me | Me | H (da, 2H), 7.25 (99, 2H), 8.94 (5, 2H); 9.08 ( 5, 1H) frequency per million "H-NMR (400 MHz, DMSO-av): b - 1.11 (5, ZN), 1.16 (5, ZN), i 1.73 (5, ZN ), 5.74 (in, 1H), 7.31 5 N Me H N 4-OSEz | Me | Me | H (yes, 2H), 7.54 (99, 2H), 8.95 (5, 2H); 9.07 (5.1H) frequent. per million "H-NMR (400 MHz, DMSO-abv): b - 1.11 (5, ZN), 1.16 (5, ZN), i 1.73 (5, ZN), 5.78 ( 5, 1H), 7.58 11 5 N Me Н H 4-5С0Ez | Me | Me | H (yes, 2H), 7.65 (99, 2H), 8.95 (5, 2H); 9.07 (5, 1H) frequency per million "H-NMR (400 MHz, DMSO-av): b - 0.92 (5, 9H), 4.23 (а, 9-10

Hz. 2H), 7.35 (y, 9-8 Hz, 2H), 8.83 (5, 2H), 9.04 (5, 1H) freq. per million "H-NMR (400 MHz, DMSO-abv): b - 1.23 (5, ZN), 1.24 (5, ZN), 13 | 5 | n |i-propinl! NO) no) 4Osez|Me|Me nH and daotives of No (5, 2H); 9.13 (5, 1H) parts per million

Table 1 in" d? and in y--

St. in the day. 7

Ma, Ma () m| XA in | vv |-USRV|vV|vVi|vV | 49 (/// Physical data/Z "H-NMR (400 MHz, DMSO-abv): b - 1.14 (5, ZN), 1.38 (5, ZN), 14 HO | ispropynl| HO) no) 4osez | Me | Me | H and dao tovi Nv (5, 2H); 9.13 (5, 1H) often on

Mill. "H-NMR (400 MHz, DMSO-av): b - 1.26 (5, ЗН), 1.27 (5, ЗН), иБ| 8 | n |i-propynl/. HO| no) 4- 5Sez|Me|

Mill. "H-NMR (400 MHz, DMSO-abv): b - 1.15 (5, ЗН), 1.28 (5, ЗН), 2.80-2.88 (t, 1Н), 3.10- 3.22 167| 8 | H -propenyl. NO| no 4-5Sez | Me | Me | H Tv) BEOB2 (t, i) BO 5.85 (t, 1H), 7.57 (ai, 2H), 7.68 (a9, 2H), 8.86 (c, 2H); 9.02 (5, 1H) parts per million "H-NMR (400 MHz, DMSO-av): b - 0.91 ( z, 9H), 4.28 (a, 9-10

Hu, 1H), 4.91 (a, 9-10 Hz, 1H), 17 N IVy Н H 4-5SEz Н Н H 15.61 (5, 1H), 7.07 (a, 9-7 Hu, 2H), 7.60 (y, 9-7 Hz, 2H), 8.84 (5, 2H), 9.05 (5, 1H) freq. on

Mill. "H-NMR (400 MHz, DMSO-abv): b - 0.11 (t, 2H), 0.32 (t, 2H), 0.95 (z, ЗН), 4.16 (4,

U-10 Hz, 1H), 4.74 (a, 9-10 18 N Mor N noryaost o no no no|duyanu vv, n), 706 (9, 9-9 Hz, 2H), 7.28 (y , 9-9 Gu, 2H), 8.89 (5, 2H), 9.09 (5, 1H) frequent. per million 1e|o|nu| could | n | n | 48 | but but noMsoezzoviMenNr-ZY! "H-NMR (400 MHz, DMSO-α): b - 0.89 (t, 1H), 1.12 (t, 1H), 1.45 (t, 1H), 1.57 (t, 1H) , 4.44 (a, 9-10 Hz, 1H),

Н SSR Н Н 4-OSEz Н Н Н 4.74 (9, 9-10 Hz, 1Н), 6.31 (5, 1Н), 7.10 (а, 9-7 Hz, 2Н), 7.29 (а , 9-7 Hu, 2H), 8.98 (5, 2H), 9.17 (5, 1H) frequent. per million

Table 1 to d? Uh uh--

St. in the day. 7

Ma M -y (I)

Me! XA in || in |-sSeVivV|vVu|nVi| 5 49(/// Physical data "H-NMR (400 MHz, DMSO-abv): b - 0.88 (t, 1H), 1.11 (t, 1H), 1.47 (t, 1H), 1 ... (5, 1H), 7.15 (a, 9-9 Gu, 2H), 7.64 (y, 9-9 Hz, 2H), 8.99 (5, 2H), 9.15 (5, 1H ) frequency per million "H-NMR (400 MHz, DMSO-abv): b - 1.04 (5, ZN), 1.34 (5, ZN), 1.70 (5, ZN), 5, 76 (5, 1H), 6.87 227 N Me Н H 3-OSEz | Me | Me | H (|(Bbg5,1H), 6.95 (rga, 1n), 7.05 (rga, tn), 7.38 (y, 1H), 8.94 (5, 2H); 9.07 (5, 1H) parts per million "H-NMR (400 MHz, DMSO-av): b - 1.04 ( 5, ЗН), 1.34 (5, ЗН), 1.70 (5, ЗН), 5.76 (5, 1Н), 6.87 Me | H (|(Bbg5,1H), 6.95 (rga, 1n), 7.05 (rga, tn), 7.38 (y, 1H), 8.94 (5, 2H); 9.07 (5, 1H) frequency per million "H-NMR (400 MHz, DMSO-abv): b - 0.91 (а, ЗН), 0.97 (а, ЗН), 1.09 (5, ЗН ), 1.11-1.21 (t, x ! 1H), 1.91 (5, ЗН), 6.98 (horn 5, 24 H iIRg Н H 3-OSEz | Me | Me | Н 1Н), 7.05 (bga, 1H), 7.09 (run 9, 1H), 7.42 (I, 1H), 9.01 (5, 2H), 9.07 (5, 1H) frequency per million "N -NMR (400 MHz, DMSO-av): b - 1.10 (5, ЗН), 1.31 (5, ЗН), 1.72 (c, ЗН), 5.78 (5, 1Н),

H Me H H 2-OSEz | Me | Me | H 1|7.14-7.21 (t, 2H), 7.27-7.31 (t, 1H), 7.35 (0, 1H), 8.88 (5, 2H); 9.05 (5.1H) frequent. per million "H-NMR (400 MHz, DMSO-abv): b - 1.10 (5, ЗН), 1.40 (5, ЗН), 26 Н |1-propynyl Н Н 2-OSEz | Me | Me | H 11.58 (5, ZN), 7.01-7.39 (t,

AN), 8.95 (in, 2H), 9.11 (5, 1H) frequent. per million "H-NMR (400 MHz, DMSO-av): b - 0.91 (а, ЗН), 0.98 (а, ЗН), х! 1.08 (5, ЗН), 1.33 (in, ЗН), 27 H iRg Н H 2-OSEz | Me | Me | H 263-270 (t, 1H), 7.18-7.40 (t, 4H), 8.99 (in, 2H) 9.07 (5.1H) parts per million

Table 1

V' in Y in y-- 1 in He dz E di. 7

Ma», M -y (I) m/min in |v. in |-mSeV'|vn|vne|vV| 4 years of Physical Science /-- 28 o'clock you | no no loss iooR 3.40 1, (MeNY-373 seGo|ni| yiv 12 no| los sor ZAT y, IMHNESZV zo1o| no yiv ((»te| no lose sor 3.59 IMUNK-Z71 zoni t ze no| IMENK-407, IMENK-407, IMENK-407, IMENK-407, IMENK-387, IMENK-387, 2/2 (MeNE-405 | but nou aosen iooR 2.63 1, I(MeNI"-339 x for comparison

Me - methyl, iRg - isopropyl, IVy - tert-butyl, SSR-1-chlorocyclopropyl, MCP-1- methylcyclopropyl

The values of Is9P were measured in accordance with the EEC Directive 79/831 Annex MAV by HPLC (high performance liquid chromatography) on a reversed phase column (C 18) using the methods below:

Ia LC-MS determination in the acidic range was carried out at pH 2.7 with 0.195 aqueous formic acid and acetonitrile (containing 0.1 96 formic acid) as mobile phases; linear gradient from 10 95 acetonitrile to 95 95 acetonitrile.

Examples of use

Example A: Zrpayegoipesa test (cucumber) / protective

Solvent: 49 parts by weight of M, M-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young cucumber plants were sprayed with the preparation of the active compound in the specified application rate.

One day after treatment, plants were inoculated with a spore suspension of 5rpaegoipes pMiidipea.

After that, the plants were placed in a greenhouse at a relative humidity of air and a temperature of 23 "С.

It was evaluated 7 days after inoculation. 0 95 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table A

Zrpaegoipesa test (cucumber) / protective

G.I. of ShK is poten per million)

SNU is not on 2" m about BOYU shshch

M OSE,

Table A

Zrpaegoipesa test (cucumber) / protective 000zhenneyutyu 000 deeveeeetya eroptnste per million)

SN" not OH 3 m WITH 94 shshch

M ZSE, not SNU not OH 4 m 5 5OO 91 shsh

M SE ns Sn, not OH 7 2 5OO 95

WITH

M SE

IS

E on 5BOO 100

M o is

M SE ns ON o 9» M | 5OO 95 (. ns sn,

M OS, not on OS 22" uh with 500 95

Her ns sleep, not SNU not he 12 m at 5OO 100 shshch

M OS, no

ХХ on 13 m Z 5OO 76 (. | ns sn,

M OS,

Table A

Zrpayegoipesa test (cucumber) / protective ns sh

ХХ on 14 m o 5О0 95 (5 M ns sn,

M OSE, ns F xx on 23 2 OSE" BYU 88 i- us sn, not ho

XX on m 5 5OO 88 (- Sh ns sn,

M ZSEz

СН» n- on 247 m o OS 5О0 83 we sleep

SN" ne- on OS, 27 m o 500 88 we sleep no sleep no-M on 17 m "oh 5OO 95 h- in ZSEz nen 18 m o 5OO 95 - sia OSE, ploma fl 19 me o BOYU 95 shsh

M ZSE with

Table A

Zrpaegoipesa test (cucumber) / protective

Gyaennsyu 0000 ebnveeenitdotnenst per million) si on m o 5OO 75 shsh

M OSE, si on 21 m o BOYU 100 shshch

M ZSEa not SNU not On SI 29 m o 5OO 100 shshch

M OS, ns Sn. not he SN, 3o m o BOYU 100

WITH

M OSE, not Sn, not OH 31 m o shch 5OO 100 shshch

M ZSEa not SNU not he 32 m o SN» 5OO 95 shshch

M ZE not Sn, not he 33 m o BOYU 95

WITH

M 80, SE not Sn, not he 34 m o 5OO 95 shshch

M OSE, N x for comparison

Example B: AKegpagia test (tomato) / protective

Solvent: 49 parts by weight of M, M-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young tomato plants were sprayed with the preparation of the active compound in the specified application rate. One day after treatment, the plants were inoculated with a suspension of APKetagia 5oYapi spores and then left at 100 9o rel. humidity and 22 °C for 24 hours. After that, the plants were left at 9695 relative atmospheric humidity and a temperature of 20 °C. The evaluation is carried out 7 days after inoculation. 0 9o means an efficiency corresponding to that of the control, while an efficiency of 100 95 means that no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table B "AKegpagia test (tomato) / protective te olnnenno00 DeNEEUNK voi per million)

SN. not he 2» m o 5OO 100 shshch

M OSE,

SN. not he 3" m 5 5OO 95 shshch

M ЗСЕї not СНі not on 4 m З 5ОО 95 shshch

M ZSE' not SN" not he 7 7 500 94 shshch

M ZSE'

IS

IS

HE FIGHTS

M o is

M ZSE'

Table B "AKegpagia test (tomato) / protective (yayu 000 (teveenet vrettyutst per million) not on 9» M | 5OO 100 (. Not sn.

M OSE, ns on o OSE 22 uh with BO 100 yv ns sn, not on OSE, o 25" uh 500 s ns sn, ns on 8 10" M | 5OO 100 (in Ne sn.

M OSE, ns on 8 (- Sh ns sn,

M SE ns Sn, non-M on 12 m o BYU 100 shshch

M OS, no

ХХ on 13 m WITH 100 BATTLE

I I ns sn,

M OS, no

ХХ on 14 m at 5О0 94

I. | us dream

M OS" no

ХХ on 23 m o OSE» 5ОО0 75 i- us sleep

Table B "AKegpagia test (tomato) / protective

I YN ev NOT per million) no

XX on m Z BOYU 94 (- no sn,

M ZSE with

SN» ns on 24 m o OS 5О0 95 - carries sn

Lo sn,

But he - 5 16" iy | IF 5OO 100 - not sn m ZO» not Sn, not ON 17 m o BOYU 94 shsh

M ZSE with nen 18 m o 500 i-

M OSE, net YN 19 m o 5O0 shshch

M ZSEz si on m o 5OO 100 i-

M OS, si on 21 m o BOYU 95 shshch

M ZSE with

Table B "AKegpagia test (tomato) / protective eG00leniyayutyao 0000 eeveeenetykroptenst s per million.) ns SN ne on SI 29 m o BOYU 78 shsh

M OSE, not SN» not on SN» zom o 5OO shshch

M OSE, not SN" not he

With a power of 5OO 95 shshch

M ZSE not SNa not he 33 m o BOYU

WITH

M ZO,SE, not SN not on 34 m o 5OO 95 shshch

M OSE, N x for comparison

Example C: I eriozrpayegia podogyt test (wheat) / protective

Solvent: 49 parts by weight of M, M-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young wheat plants were sprayed with the preparation of the active compound in the specified application rate.

One day after treatment, the plants were inoculated with an aqueous suspension of spores of Eriozrpaegia podogyt and then left at 100 95 relative atmospheric humidity and 22 "C for 48 hours. After that, the plants were placed in a greenhouse at 90 95 relative atmospheric humidity and a temperature of 22 "C. The assessment is carried out 7-9 days after inoculation. 0 96 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table C

And eriozhrpayetia podogyt test (wheat) / protective

NI nin ia NEO per million) sno n- on 2" m o BOYU 100

WITH

M OS, sn, ne- on 3" m 5 5OO shshch

M ZSE with non-SNU non-M on 4 m 5 5OO 70 shsch

M ZSEz not Sn, non-M on 7 m 5OO 95 shshch

M ZSEz not he o 9» M | 5OO 100 (. Sh ns sn,

M OS, not on OSE 22" uh with BO 100 and ns sn. not him

WITH

10" M | 5OO 100 (. ns sn.

M OSE, not him

WITH

11" M | 5OO 95 (5 Sh ns sn,

M ZSEz ns Sn, n-M on 12 m o BOYU 95 shsh

M OS,

Table C

And eriozhrpayetia podogyt test (wheat) / protective 100yaennsyutyu 000 deeveeetya eroptnste per million.) no

ХХ on 13 m WITH BOYU 95 (E | ns sn.

M OS, no

ХХ on 14 m at 5OO 100

I. | us dream

M OS, no

ХХ оон 23 m (in, Osn, 5OO 70 и- us sn, no

ХХ on m 5 BYU 95

I. not Sn,

M ZE sn. ns on 24 m o OS 5О0 i- us sleep nos ОН d 5 16" M | 5О0 70 (. not sn,

M ZSEa not CH, not OH 17 m about BOYU 94 shshch

There is no M 5SE 18 me o 5OO 95 shshch

M OS,

Table C

And eriozhrpayetia podogyt test (wheat) / protective eH00yaennyyutyao 0000 eeveeenyakroptenst s per million.) netu 19 m o BOYU 95 shsh

M 5SE,

SI on 20 m at 5OO 95

IS

M OSE, not SN" not on SI 29 m o 5OO 75 shshch

M OSE, ns СН ne he СН» zo m o BOYU

WITH

M OSE, not SN not him

With a power of 5OO 95 shshch

M 5SE, not SN" not on

With 3 m at 5OO 94

IS

M 5О,СЕ, not СНi not on 34 m o 5ОО 100 shsh

M OSE, N x for comparison

Example 0: Mepishgia test (apple tree) / protective

Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. After spraying, the coating was dried, the plants were inoculated with an aqueous suspension of conidia of the apple scab pathogen Mepinpgia ipaedzaii" and then left in an incubation booth at approximately 20 "C and 100 95 relative humidity for 1 day. After that, the plants were placed in a greenhouse at approximately 21 "C and relative atmospheric humidity of about 90 95. The assessment was carried out days after inoculation. 0 90 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed. 10 In this test, the following compounds according to the invention showed, at a concentration of the active compound of 100 parts. per million, efficiency 70 95 or more:

Table Yu

Mepishpgia test (apple tree) / protective eG0oyaenyatyuta 000 reenneovyatesiabdroptenst s

SNU not on 2" m about 100 94 shshch

M OS, not he (c) OSE 22» M Y 100 94 (- ns sn,

M not he (c) 9» M | 100 94 (. not sleep,

M OSE, no Sna no on 12 m o 100 shshch

M OSE, not SN" not on 17 m o 100 100 shshch

M 5SE, neth un 18 m at 100 shshch

M OSE,

Table Yu

Mepishpgia test (apple tree) / protective eGyaeniatyuta 000 reenneovyatesyabdroptenst s

SI (on! 20 m at 100 100 shsh

M OS, not Snuz not on SN" z o m o 100 shshch

M OSE, not SN" not he

With a power of 100 shshch

M ZSE' not SnNua not he 33 m o 100

WITH

M ZO, SE, x for comparison

Example E: Ogotusez test (beans)/protective

Solvents: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, a part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. After spraying, the coating was dried, the plants were inoculated with an aqueous suspension of spores of the pathogen of leguminous rust Ogotusez arrepaiscia" and then left in the inoculation booth at approximately 207 and 100 95 relative atmospheric humidity for 1 day. After that, the plants were placed in a greenhouse at about 21 C and a relative humidity of about 90 95. The assessment was carried out 10 days after inoculation. 0 956 means an efficiency corresponding to that of the control, while an efficiency of 100 Fo means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of the active compound of 100 parts. per million, efficiency 70 95 or more:

Table E

Ogotusez test (beans)/protective mofenyasyutie 000000 (aries then no today sleep, no- he 2 Im o 100 100

Io

M OS, ns ON o 9" uh "Fi 100 100 - not sn m OS, not SN» non-M on 12 | at 100 100 shshch

M OS, not SNU non-MH on 17 Im o 100 100

Io

M SE no 18 Goes at 100 100

WITH

M OS, si on m o 100

WITH

M OS, not SN» not on SN» m o 100 100 shshch

M OS, no Sleep no-M on 3 12 o s 100 100

WITH

M ZSE,

Table E

Ogotusez test (beans)/protective to Iennesylyu 0000000 fo vnevnia Ken edostvnt s ne SNa ne he 33 | at 100 100

WITH

M ZO, SE, x for comparison

Example E: ViIshtegia dgatipi5 test (barley) / protective

Solvent: 49 parts by weight of M, M-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. After spraying, the coating was dried, the plants were dusted with Vishtegia dgatipov spores 7.5 years. okay

Plants were placed in a greenhouse at a temperature of about 18°C and a relative humidity of about 80 95 to promote the development of powdery mildew pustules. Scored 7 days after inoculation. 0 96 represents an efficiency similar to that of the control, while an efficiency of 100 95 means that no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table EE

Vishtegia dgatipi5 test (barley) / protective eH00lenyuyaomn 000 Deeveeniatiao eroptenst si per million.

SNU not on 2 m o 5OO 100

WITH

M OS, sn. not he 3" m 5 5OO 100

Io

M ZORE" not Sna not he 4 m WITH BATTLE

WITH

M ZORE,

Table EE

Vishtegia dgatipi5 test (barley) / protective e70lenyasyutn 000 Daily dtnenst o per million.) not on o 9» M | 5OO 100 (. not sleep,

M OSE, not Sn, not he 12 m o BOYU 100 shshch

M OSE, no

ХХ он 14 Мо БОЙ 100 (. | us sn,

M OS, not SNU not he 17 m o BOYU 100

Io

M 5SE, he is not 18 m o 5OO 100 shshch

M OSE, on ns 19 m o BOYU 100

WITH

M 5SE, not SNU not on SN» zom o 5OO 100 shshch

M OS, not Sn, not he 33 m o BOYU 100

WITH

M 50, SEz x for comparison

Example 0: Zeriogia Igysi test (wheat) / protective

Solvent: 49 parts by weight of M, M-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. After spraying, the coating was dried, and the plants were sprayed with a suspension of 5eriogia igikisi spores.

The plants were left in the incubation cabin at 202С and 100 95 relative atmospheric humidity for 48 hours. After that, the plants were placed under the penetrating light of the cap at 15 "C and 100 95 relative humidity for an additional 60 hours. The plants were placed in a greenhouse at a temperature of about 15 "C and a relative atmospheric humidity of about 80 95. They were evaluated 21 days after inoculation. 0 95 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table C zerogia igiysi test (wheat) / protective

Goyan turf rtents

SN. not he 2 m o 5OO 93 shshch

M OSE,

SN. not he 3" m 5 5ОО 75 shshch

M ZSEh not SNh not he 4 m WITH BOYU 100 shshch

M ZSE' not he c) 9» We | FIGHT (- ns sn,

M OS, no Snuz no on 12 m o 5OO 100 shshch

M OSE,

Table C seriogia igiysi test (wheat) / protective eG0oyaenyasyuta 000 reenneovyatesiabdroptenst s ne

ХХ он 14 ме ів) 5ОО

M OS, not SN" not he 17 m about BATTLE 100 shshch

M ZSE' neth un 18 m o 5OO 100 shshch

M OS, tribe fl 19 m o 5O0 shshch

M ZSE ne Sna ne he SN," z o m o 5OO 7 shshch

M OSE, x for comparison

Example H: Rissipia ygyisipa test (wheat) / protective

Solvent: 49 parts by weight of M, M-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. After spraying, the coating was dried, and the plants were sprayed with spores from a spore suspension of Rissipia ipiisipa. The plants were left in the incubation booth at 20 "C and 10095 relative atmospheric humidity for 48 hours. The plants were placed in a greenhouse at a temperature of about 20 "C and a relative atmospheric humidity of about 80 95. They were evaluated 8 days after inoculation. 0 90 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of 500 parts of the active compound. per million, efficiency 70 95 or more:

Table N

Rissipia igyisipa test (wheat) / protective 0yazhyuyutyu 00 | beeeeeenya | eootyunstya (fr. per million)

SN" not on 2" m o BOYU 100 shshch

M OS, not on c) 9" uh, Ffi 5OO 100 - not sn m OSE, not Snuz not OH 12 m o 5OO 100 shsh

M OSE, no

XX on 14 still iv) 5OO

And her sleep,

M OSE, not SN not he 17 m o BOYU 100 shshch

M 5СЕа no 18 m o 5ОО 100 shshch

M OSE, prom fl 19 me o BOYU 100 shshch

M ZSE, not Sna not he SN," 3 o m o BOYU 100 shsh

M OS,

Table N

Rissipia igyisipa test (wheat) / protective

Active compound Application rate Effectiveness (95) (fr. per million) no SnNua no on 33 ma o BOYU 100

WITH

M ZO, SE, x for comparison

Example I: RpaKorzoga raspugpigi test (soy) / protective

Solvent: 28.5 parts by weight of acetone

Emulsifier: 1.5 parts by weight of polyoxyethylene alkylphenyl ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. One day after spraying, the plants were inoculated with an aqueous suspension of spores of the soybean rust pathogen (RpaKorzoga raspugpigi). The plants were placed in a greenhouse at a temperature of about 202C and a relative humidity of about 80 95. They were evaluated 11 days after inoculation. 0 95 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

In this test, the following compounds according to the invention showed, at a concentration of the active compound of 100 parts. per million, efficiency 80 95 or more:

Table

Rpakorzoga raspugpigi test (soy) / protective eG0oyaenyatyuta 000 reenneovyatesyabdroptenst s ne Sna ne on 12 m o 100 shsh

M OSE, not SN" not on 17 m o 100 97 shshch

M ZSE not (he! 18 m at 100 shshch

M OS,

Example in): Rugeporpnoga yegez test (barley) / protective

Solvent: 49 parts by weight of M, M-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the specified amounts of solvent and emulsifier, and the concentrate was diluted with water to obtain the desired concentration. To test the protective activity, young plants were sprayed with the preparation of the active compound in the specified application rate. 1 day after this treatment, the plants were inoculated with an aqueous suspension of spores of Rugeporpoga iegev.

The plants were left in the incubation cabin at 20 "С and 100 95 relative atmospheric humidity for 48 hours. The plants were placed in a greenhouse at a temperature of about 20 "С and a relative atmospheric humidity of about 80 95. The assessment is carried out 7-9 days after inoculation. 0 95 means an efficiency corresponding to that of the control, while an efficiency of 100 95 means no infection was observed.

Table

Rpakorzoga rasputi?i test (soy) / protective per million)

SNU not on 500 2 M o (E 100

M OS, no Sleep no on 500 95 12 ke o i- 100 (610)

M OS, x for comparison

Claims (11)

FORMULA OF THE INVENTION 1. Pyrimidine derivatives of formula (I) E Kb ro ko U ik E! х в2 3 и Е7 и Mod im ; (I) in which X is 0, 5, 50, 5O", -CH"g- or is a single bond, VE is methyl, A" is tert-butyl, 1-propynyl, 1-chlorocyclopropyl . C4-haloalkyl, Vo and KU are the same or different and represent in each case hydrogen, halogen, C1-Ca4- alkyl or C-C--haloalkyl, or together represent the group -СНо-СН»- so that, together with the carbon atom to which they are attached form a cyclopropyl ring, B" is hydrogen, halogen, C1-C-alkyl or C-C4-haloalkyl, and their agrochemically active salts. Zo 2. Pyrimidine derivatives of formula (I) according to point 1, where X is 0, 5, CH" or is a simple bond. BE is methyl, A is tert-butyl, 1-propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, /1-methylcyclopropyl or 2,4-difluorophenyl, B? and C in each case are hydrogen, Y is O or 50, B" is hydrogen, fluorine, chlorine or C:1-C12-haloalkyl, B? and 25 are the same or different and each is hydrogen, fluorine, chlorine, bromine, iodine, C1-Ca4-alkyl or C1-C--haloalkyl, or together represent the group -"CH"-CHe-, B" represents hydrogen, fluorine, chlorine, bromine, C1i-Ca-alkyl or Ci-Co-haloalkyl. 3. The method of combating phytopathogenic harmful fungi, which differs in that the pyrimidine derivatives of formula (I) according to point 1 or 2 are applied to phytopathogenic harmful fungi and/or their growth sites. 4. A composition for the control of phytopathogenic harmful fungi, characterized in that it contains at least one pyrimidine derivative of formula (I) according to item 1 or 2, together with excipients and/or surfactants. 5. Application of pyrimidine derivatives of the formula (I) in accordance with point 1 or 2 to combat phytopathogenic harmful fungi. 6. The method of obtaining compositions for combating phytopathogenic harmful fungi, which is characterized by the fact that pyrimidine derivatives of the formula (I) according to item 1 or 2 are mixed with fillers and/or surface-active substances. 7. The method of obtaining pyrimidine derivatives of the formula (I) according to item 1 or 2, which differs in that either (A) oxirane derivatives of the formula (II) t 5 M (I) in which B' represents tert-butyl, 1- propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl or 2,4-difluorophenyl, react with (thio)phenols of the formula (I) E in , (in Zo in which X represents 0, 5, 50, 5O", -CHn- or represents a simple bond, B2 and EZ in each case represent hydrogen, U represents 0, 5, 50 or 50", "B" represents hydrogen, fluorine, chlorine or C:-C4-haloalkyl, thereby obtaining pyrimidine derivatives of the formula (1-a) in which X, K", B, BZ, Y and E" have the meanings indicated above; or (B) ketones of the formula (IM) E Kb vo x v2 3 y o (M) in which X, B", B, BZ, U and E" have the values specified above, B? and 29 are the same or different and represent in each case hydrogen, halogen, C1-Ca4-alkyl or C.i-C--haloalkyl, or together represent the group -СНо-СНе- so that, together with the carbon atom, to to which they are attached, form a cyclopropyl ring, react with pyrimidinyl halides of the formula (M) Na! Hey and Maiu M na m) in which B" is hydrogen, halogen, C1-C--alkyl or C-C4-haloalkyl, Nai is halogen, thus obtaining pyrimidine derivatives of the formula (1-5) ДН ЕЕ х в2 В и Гей и Мою М na iv) in which Х, К", 8-2, ВЗ, У, В" and КЕ" have the values indicated above; or (C) bromides of the formula (MI) and (c) 5 - Вг M xx y " (M) in which РЕ" and РУ have the values specified above, react with (thio)dphenols of the formula (1) E Da nXx E With Mo (M) in which X, Kg, BZ, U and E" have the values indicated above, thus obtaining ketones of the formula (MI) E b ro U where (c) х в2 В и щ My M va M) in which X, B, VU, M, VU, A» and K5 have the values indicated above, which are then subjected to reactions with organometallic compounds of the formula (MI ) in -M (mM) in which B' has the values indicated above, M is a metal, thus obtaining pyrimidine derivatives of the formula (1-c) b vro i no - EE x v2 3 i i Myu M Ba ; (I-c) in which X, K", 82, VAZ, U, VU, V and KE have the values indicated above; or then (C) pyrimidine derivatives of the formula (1-5) E in c) DN EE x in2 in and Hei and M M schi (5) in which X, KK", 82, VZ, M, VU, B", A5 and K/ have the values indicated above, react with halides of the formula (IX) in which De represents is alkyl, trimethylsilyl, formyl or acetyl, Na! represents chlorine or bromine, thereby obtaining pyrimidine derivatives of the formula (1-4) VU, B, Nei EE" have the meanings specified above. 8. Oxirane derivatives of the formula (II-a) TA o Kk M ko y ; (P-a) in which Vya is 1-propynyl or 2,4-difluorophenyl. 9. Ketones of the formula (IM-a) ovriv E v te U -Ke v x E v2v vv o , (M-a) in which XB is 0, BZ is tert-butyl, 1-propynyl, 1-chlorocyclopropyl . are the same or different and represent in each case hydrogen, halogen, C1-Cα-alkyl or C-C--haloalkyl, or together represent the group -СНо-СН»- so that, together with the carbon atom to which they are attached , form a cyclopropyl ring. 10. Ketones of the formula (IM-B) VS ros E s o U -e s x E ros do o M (M-v) in which ХУ is 5, 50, 50», ВЕ is 1-propynyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl or 1-methylcyclopropyl, where des and v3c are in each case hydrogen, Us represents 0, 5, 50 or 50", Vis represents hydrogen, fluorine, chlorine or Ci-C4-haloalkyl, Wes and CS are the same or different and represent in each case hydrogen, halogen, C1-Ca4-alkyl or C-C--haloalkyl, or together represent the group -СНо-СН»- so that, together with the carbon atom to which they are attached, forming a cyclopropyl ring. 11. Bromides of the formula (MI-a) va (c) VA -- Vg M xx y " y Ma) Zo in which VA is a halogen or C-Ca4-haloalkyl, VA is a halogen or C.1-Ca-haloalkyl .