UA48114C2 - Substituted azadioxacycloalkenes, a process for their preparing, fungicidal agents on the basis of the substituted azadioxacycloalkenes and a process of their producing - Google Patents

Abstract

New azadioxacycloalkenes hive the formula (I), in which A stands for optionally substituted alkane diyl (alkylene); Ar stands for optionally substituted arylene or heteroarylene; E stands for one of the following groupiags (a), (b), (c), (d), (e) where Y is oxygen, sulphur, methylene (CH2) or alkylimino (N-R); and Z - G stand for various substituents. Also disclosed are a process for preparing tne same and their use as fungicides.

Description

Description of the invention

It is known that certain substitutions of 5,6b-dihydro-1,4,2-dioxazine have fungicidal 2 properties (see the application of OR Mo01221371, mentioned in Spet. Abzigasiv 112, abstract 98566; patent OR

Mo02001484, mentioned in Spet. Abvigasiv 113, abstract 6381U).

However, these compounds did not acquire special significance.

Now they beat Naydan! new substitution of azadioxacycloalkeny of general formulas!

I dya A in ki

EE about I0) where

A - unsubstituted or substituted alkanediyl (alkylene),

Ag - unsubstituted or substituted arylene or heteroarylene,

E - 1-alkene-1,1-diyl having a radical B in position 2, 2-aza-1-alken-1,1-diyl having radical 22 in position 2, 3-oxa- or 3-thia-1 -propene-2,3-diyl, having a radical B in position 1,

3-aza-1-propene-2,3-diyl, having radical K in position C and radical B in position 1, 1-aza-1-propene-2,3-diyl having radical 22 in position 1, З- oxa- or 3-thia-1-aza-propene-2,3-diyl, having a radical c in position 1, 1,3-diaza-1-propene-2,3-diyl having a radical K and c in position 3 position 1 radical B? or an unsubstituted or substituted imino group (, azamethylene", M-B Y), and B means alkyl, K! - hydrogen, halogen, cyano or an unsubstituted or substituted alkyl, alkoxy, alkylthio-, 1 alkylamino- or dialkylamino group, 22 - hydrogen, amino, cyano or unsubstituted or substituted alkyl, cm alkoxy, alkylamino- or dialkylamino group, BZ - hydrogen, cyano or unsubstituted or substituted alkyl, i) alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

Со is a single bond, oxygen, unsubstituted or substituted by halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl, alkanediyl, alkenediyl, oxalkenedyyl, alkynediyl, or one of the following groups -0-СО0-, -СО0-0-, - "СН2-0-, -0-СНо-, -СО-0-СНо-, "СНо-9-С9-, -0-20-СНо-, 0-20-0-СНо-, -МеМ-, ( Od, -СНо-8(О)п-, -СО-, -8(О)п-СНо-, -С(Б3-М-О-, -С(Б73-М-О-СНо-, -Щ (5)-, -СО-Щ(Б5)-, -Щ(5)-сО-, -4-сСО-М(5)А,07 -М-ФЭ(27)-0-СНо-, СсНо- О-М-С(87)-, -М(5)-с0-9-, СО-М(5)-сО-0-, -М(Б5)-СО-0-СНо-, -СО-СНо - or "- -MEM-C(B -M-O-), and n means the number 0, 1 or 2, 0 - oxygen or sulfur, Bi - hydrogen, cyano, or unsubstituted or substituted alkyl, alkoxy, alkylthio-, acylamino-dialkylamino group or

Z is cycloalkyl, K5 is hydrogen, hydroxyl, cyano, or unsubstituted or substituted alkyl, alkoxy, or cycloalkyl, and 7 is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heterocyclyl.

In addition, it was found that a new substitution of azadioxacycloalkene of general formulas! (I) it is possible to "obtain due to the fact that a) the production of carboxylic acid of the general formula (II) With c 2. And (8) -A KG :" with i "where i" Ag, E, b and 7 have the above meaning, a

K means alkyl, in the first stage it is subjected to interaction with hydroxylamine or its (ee) halide salt, if necessary, in the presence of an acid acceptor and, if necessary, in the presence of a diluent, and in the second stage in situ, i.e. without an intermediate separation of the reaction product of the first stage, subjected to interaction with two-substituted alkanes of the general formulas! (III) - X-A-X (I)

Where am I?

A has the above-mentioned meaning, i

X means halogen, alkylsulfonyloxy or arylsulfonyloxy, if necessary, in the presence of an acid acceptor and, if necessary, in the presence of a diluent, or, as in b) in the case, if in formula (I) b means oxygen or the group -CHН-О-, and A, Ag, E and 7 have the above-mentioned meaning, hydroxyaryl compounds of the general formula (IM) dk Ag m-o nat -« -A vo o 1 where

A, Ag and E have the above-mentioned meaning, interact with compounds of the general formula (M) 7-(СНо)хх (М) b5 where

X and 7 have the above-mentioned meaning, and t means the number 0 or 1, if necessary, in the presence of an acid acceptor! and, if necessary, in the presence of a diluent, with the subsequent, if necessary, translation of group 7 into the desired value by ordinary methods, or, that c) in the case, if in formula (I) C means the group -0-CH»-, and A, Ag, E and 7 have the above-mentioned meaning, halomethyl compounds of general formulas! (MI) 779 he in - ;A mu 70 o gde

A, Ag and E have the above-mentioned meaning, and

X! means halogen, exposed to interaction with compounds of general formulas! (MY) 75 7-9-H (MI) where

OO and 7 have the above-mentioned meaning, if necessary, in the presence of an acid acceptor! and, if necessary, in the presence of a diluent, or, that d) hydroxyalkoxyamides of general formulas (MIP) no.

M And not he (washed with where o

A, Ag, E, b and 7 have the above-mentioned meaning, undergo cyclization with a water-removing agent, if necessary, in the presence of a diluent.

It was found that there is a new substitution of azadioxacycloalkeniya of general formulas! (I) have a very strong fungicidal effect. "

The proposed compounds can be obtained as mixtures of various isomeric forms, in particular, E- and "-7-isomers. Both E- and 7-isomers are used, as well as mixtures of these isomers in any form.

The object of the invention is preferably compounds of formula (I), where "--

A means alkanediyl with 1 - carbon atoms, unsubstituted or substituted by halogen, alkyl or haloalkyl with 1 - 4 carbon atoms,

Ag - unsubstituted or substituted phenylene or naphthylene, or heteroarylene with 5 or 2 ring members, of which at least one represents oxygen, sulfur or nitrogen, and, if necessary, one or two more represent nitrogen, and the possible substituents used are selected from a group including: halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, unbranched or branched alkyl, alkoxy, alkylthio group, alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon atoms, unbranched or branched alkenyl, alkenyloxy or alkynyloxy, each with 2 to 6 carbon atoms, unbranched or branched haloalkyl, haloalkyl, or haloalkylthio group, haloalkylsulfinyl or haloalkylsulfonyl, each with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, unbranched or branched haloalkenyl or haloalkenyloxy, each with 2-b carbon atoms and 1-13 identical or different by various halogen atoms, unbranched or branched alkylamino, dialkylamino, o alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl, each with 1-b carbon atoms in separate alkyl parts, unsubstituted or at least monosubstituted by halogen substituents or various and/or sh--kU 20 unbranched or branched alkyl with 1 to 4 carbon atoms and/or unbranched or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 single or different halogen atoms, or doubly bonded alkylene or dioxyalkylene with 1 - b carbon atoms,

E is one of the following groups of wounds of Zk and MIT Y

Ф) CH M di CH Me No) where in U is oxygen, methylene sulfur or an alkylimino group

K - alkyl with 1 - b carbon atoms,

B - hydrogen, halogen, cyano or unsubstituted or substituted by halogen, a cyano group or an alkyl with 1 to 4 carbon atoms, alkyl, alkoxy, alkylthio group, alkylamino or dialkylamino, each with 1 to 6 carbon atoms in the alkyl residues, 65 B2 - hydrogen, amino, cyano or unsubstituted or substituted by a halogen, cyano group or alkyl with 1-4 carbon atoms, alkyl, alkoxy, alkylamino or dialkylamino, each with 1-b carbon atoms in the alkyl residues,

BZ - hydrogen, cyano or unsubstituted or substituted by halogen, a cyano group or alkyl with 1-4 carbon atoms, alkyl, alkenyl and alkynyl, each with 1-b carbon atoms, or unsubstituted or substituted by halogen, cyano group, carboxyl, alkyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, cycloalkyl and cycloalkylalkyl with 3 to 3 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part,

C is a single bond, oxygen, unsubstituted or substituted by halogen, hydroxyl, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms or cycloalkyl with 3-b carbon atoms, 70 alkanediyl, alkenediyl, oxalkenediyl, alkyndiyl, or one of the following groups -0-с9-, -69-0-, -СНо-0-, -0-СНо-, -2О-0-СНе-, -СН-0-С20-, -0-СО-СНе -, a-sa-a-sno-, -MeM-, -8(O)p-, "СНо-5(О)-, -СО-, -8(О14-СНе-, -С(В)- М-О-, -Фв(87)-М-ОО-СНе-, -М(В2)-, -СО-М(В2)-, -М(ВР)-сО-, -а-са-мщ (vk)-, -mes(B)-

О-СН»-, СНо-О-М-С(В")-, -М(АТ)-са-а-,. са-м(н)-са-а-, -м(НР)- са-о-СНе-, -СО-СНо- or -М-М-С(А)-М-О-, and n means the number 0, 1 or 2,

O - oxygen or sulfur,

B" - hydrogen, cyano, unsubstituted or substituted by halogen, cyano or alkyl with 1-4 carbon atoms, alkyl, alkoxy-, alkylthio-, alkylamino-, dialkylamino group, each with 1-b carbon atoms in the alkyl groups, or unsubstituted or substituted by halogen )

BZ - hydrogen, hydroxy, cyano or cycloalkyl with 3-b carbon atoms, unsubstituted or substituted halogen, cyano or alkyl with 1-4 carbon atoms, alkyl with 1-b carbon atoms, or unsubstituted or substituted halogen, cyano, carboxy, alkyl with 1 - 4 carbon atoms or 1 - 4 carbon alkyl carbonyl, 7 - alkyl with 1 - 8 carbon atoms, unsubstituted or substituted by halogen, cyano, hydroxyl, amino, (or 1 - 4 carbon alkyl, alkylthio - a group with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms or apalkylsulfonyl with 1 to 4 carbon atoms, unsubstituted or substituted by halogen, unsubstituted or substituted by halogen alkenyl and alkynyl, each with 1 to 8 carbon atoms, 00

Cycloalkyl with 3 - b carbon atoms, unsubstituted or substituted by halogen, cyano, carboxyl, "phenyl, unsubstituted or substituted by halogen, cyano, alkyl with 1 - 4 carbon atoms, haloalkyl with 1 - 4 carbon atoms, alkyl with 1 - 4 atoms of carbon or haloalkoxyl with 1 - 4 carbon atoms, alkyl with 1 - 4 carbon atoms or alkoxy carbonyl with 1 - 4 carbon atoms, unsubstituted or substituted phenyl, naphthyl or (if necessary, benzanyl) heterocyclyl with « 20 5 or 6 ring members , of which at least one represents oxygen, sulfur or nitrogen and, if necessary, one or two further atoms represent nitrogen, and the possible substituents are preferably selected from the group consisting of: :z» oxygen (instead of two geminal hydrogen atoms), halogen, cyano-, nitro-, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, unbranched or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl , each with 1 carbon atoms, unbranched or branched alkenyl or alkenyloxy, each with 2 carbon atoms, unbranched or branched haloalkyl, haloalkyl, haloalkylthio, haloalkylsulfinyl or (ee) haloalkylsulfonyl, each with 1 carbon atoms and 1-13 identical or different halogen atoms, unbranched or branched haloalkenyl or haloalkenyloxy, each with 2-6 carbon atoms or 1-43 identical or different halogen atoms, unbranched or branched alkylamino group, dialkylamino group, alkylcarbonyl, alkylcarbonyloxy

T» alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl, each with 1-b carbon atoms in separate alkyl parts, unsubstituted or at least monosubstituted with the same or different halogen residues and/or unbranched or branched alkyl with 1-4 carbon atoms and/or Unbranched or branched haloalkyl with 1-4 carbon atoms and 1-9 identical or different halogen atoms, double-bonded alkylene and dioxyalkylene, each with 1-b atoms (F. carbon, cycloalkyl with 3-b carbon atoms, heterocyclyl or heterocyclyl methyl, each with C - 7 g ring members, of which 1 - C are the same or different heteroatoms, in particular, nitrogen, oxygen and/or sulfur atoms, as well as unsubstituted or at least monosubstituted in the phenyl part by the same or different residues from groups including halogen, cyano, nitro, carboxy, carbamoyl, and/or unbranched or branched alkyl with 1-4 atoms carbon atoms and 1 - 9 identical or different halogen atoms and/or unbranched or branched alkyl with 1 - 4 carbon atoms and/or unbranched or branched haloalkyl with 1 - 4 carbon atoms and 1 - 9 identical or different halogen atoms and/or alkylcarbonyl or alkoxycarbonyl with 1 to 5 carbon atoms, phenyl, phenoxy, benzyl, phenylethyl, or phenylethyloxy.

At the same time, saturated or unsaturated hydrocarbon chains, such as, for example, alkyl, alkanedyl,

alkenyl or alkynyl are considered unbranched or branched also in combination with heteroatoms, for example, in the alkoxy, alkyl-thio- or alkylamino group.

Halogen generally means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially preferably fluorine or chlorine.

The invention relates, in particular, to compounds of formula (I), where

A - methylene or dimethyl (stan-1,2-diyl), unsubstituted or substituted by residues from the groups including fluorine, chlorine, methyl, zyl or trifluoromethyl,

Ag - unsubstituted or substituted ortho-, meta- or para-phenylene, as well as furandiyl, thiophendiyl, 7/0 pyrroldiyl, pyrazoldiyl, triazoldiyl, oxazoldiyl, isoxazoldiyl, thiazoldiyl, isothiazoldiyl, oxadiazoldiyl, thiadiazoldiyl, pyridinediyl, pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,3,4-triazindiyl or 1,2,3-triazindiyl, and the possible substituents are chosen, in particular, from groups including: fluorine, chlorine, cyano, methyl, zyl, trifluoromethyl, methoxy, ztoxy, methylthio, methylsulfinyl or / 5 Methylsulfonyl,

E is one of the following groups of tetragonal tetrads

Yii

SN di Mod: sl Mn: t where

Y - oxygen, sulfur, methylene or alkylimino,

K - methyl, ztyl, n.- or isopropyl, n.-, iso- or utor, bulyl,

IN! - hydrogen, fluorine, chlorine, bromine, cyano, or methyl, xtyl, propyl, methoxy, ztoxy, methylthio-, xtylthio-, CM methylamino-, xtylamino-, or dimethyl-amino group, unsubstituted or substituted by residues from groups that include fluorine, chlorine, cyano, methoxy and ztoxy,

IN? - hydrogen, amino, cyano, or methyl, ztyl, methoxy, ztoxy, methylamino-, ztylamino-, or dimethylamino group, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, methoxy, or ztoxy, and "

BZ - hydrogen, cyano, or methyl, xtyl, n.- or isopropyl, n.-, iso- or sec, butyl, unsubstituted or -x- substituted by residues from the group including fluorine, cyano, methoxy and ztoxy, allyl, propargyl . or ztooxycarbonyl, b o - a simple bond, oxygen, methylene, dimethylene (ztane-1,2-diyl), ztene-1,2-diyl, ztyn-1,2-diyl, unsubstituted or substituted by residues from the group including fluorine , chlorine, hydroxy, methyl, ztyl, n.- or isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or one of the following groups "-0-600-, -с0-0-, -СНа-0-, - 0-СНа-, -СО-09-СНо-, -СН»-а-са-, -09-20-СНе-, - с -0-с9-9-СНо-, -MAM-, -5(О )а-, "ОНо- (ат, -Са-, "(Оз ОНе-, -Ф(8З-М-О-, z -Ф(8)-М-0-СНо-, -М(85)- , -сСО-м(ВР)-, -М(У)-сО- . -М(8Р)-СО-0-, -СО-МЩ(А8Р)-СО-0- or -Ж(8)-СО-О- т" or СНе-, - while n means the number 0, 1 or 2, - O - oxygen or sulfur, iz" B" - hydrogen, cyano, methyl, ztyl, n.- or isopropyl, n.-, iso- or t-butyl, methoxy, ztoxy, propoxy, butoxy, methylthio-, zylthio-, propylthio-, butylthio-, methylamine-, zylamino-, propylamino-, dimethylamino- or distylamino group, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, methoxy or ztoxy, or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, carboxyl, methyl, zyl, n. - or isopropyl, n.-, iso- or butyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyanomethoxy or zoxy, or 60 cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, unsubstituted or substituted by residues from the groups including ei fluorine, chlorine, cyano, carboxy, methyl, ztyl, n.- or isopropyl, methoxycarbonyl or zoxycarbonyl, and 7 - methyl, ztyl, n.- or isopropyl, n.-, iso-, second-- or tert, butyl, unsubstituted or substituted by residues from the group consisting of fluorine, chlorine, bromine, cyano, hydroxy, amino, methoxy, ztoxy, methylthio, 65 zylthio, methylsulfinyl, zylsulfinyl, methyl sulfonyl, zylsulfonyl, unsubstituted or substituted by fluorine and/or bromine, allyl, crotonyl, 1-methyl-allyl, propargyl and 1-methyl-propargyl,

unsubstituted or substituted by residues from the group including fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, bromine, cyano, carboxy, phenyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, bromine, cyano, methyl, ztyl, n.- or isopropyl, n.-, iso-, sec.-- or tert, butyl, trifluoromethyl, methoxy, ztoxy, n.- or isopropoxy, difluoromethoxy and trifluoromethoxy, methyl, ztyl, n.- or isopropyl, methoxycarbonyl or ztoxycarbonyl.n.-, iso-, sec.- or tert, butyl, trifluoromethyl, methoxy, ztoxy, n.- or isopropoxy, difluoromethoxy or trifluoromethoxy, unsubstituted or substituted phenyl, naphthyl, furyl, tetrahydrofuryl, benzofuryl, tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, 7/0 Tetrahydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, benzimidazolyl, oxadiazolyl, thiads azolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-riazinyl or 1,3,5-triazinyl, and the possible substituents are preferably selected from the group including: oxygen (instead of two geminal hydrogen atoms), fluorine, chlorine, bromine, cyano-, nitro-, amino group, 7/5 Hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; methyl, ztyl, n.- or isopropyl, n.-, iso-, sec- or tert, butyl, methoxy, ztoxy, n.- or isopropoxy, methylthio, ztylthio, n.- or isopropylthio, methylsulfinyl, ztyl sulf nyl, methylsulfonyl or zylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, zylamino, n.- or isopropylamino, dimethylamino, distylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, zoxycarbonyl . trimethylene (propane-1,3-diyl), methylenedioxyyl, ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, unsubstituted or at least monosubstituted by mono or various residues from the group consisting of fluorine, chlorine, methyl, zyl, n.- or isopropyl , as well as phenyl, phenoxy, benzyl c g MlY benzyloxy, unsubstituted or at least monosubstituted in the phenyl part with the same or different residues from the group including fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, methyl, ethyl, n .- or isopropyl, n.-, iso-, sec.- or tert, butyl, trifluoromethyl, methoxy, ztoxy, n.- or isopropoxy, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl and ztoxycarbonyl.

A particularly preferred group of the proposed compounds are compounds of the formula (I), where "E and A is dimethyl (stan-1,2-diyl),

Ag - ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl, -

E - one of the following groups "-

Zedyat and tet so 35 sn, 1 M, "I iya v2 gde

B and 22 mean methoxy, "

Co - oxygen, methylene or one of the following groups 40 - с -СНа-о-, -0-СНо-, -5(0)4-, «СНо-В(О)п-, -5(О)4- СНо-, -С(8)-М-О-, . "» -0-MeF(VY)-, -O(AI)-M-O-СНе-, -М(А?)- or -СНо-О-МеСВ, where 45 p is the number 1, 2 or З, ve B - hydrogen, methyl or methyl, i

Ge | B - hydrogen, methyl or zyl, and from 7 - unsubstituted or substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, and possible substitutes chosen from groups including -k 70

Im fluorine, chlorine, bromine, cyano, methyl, ztyl, n.- or isopropyl, n.-, iso-, sec, or tert, butyl, methoxy, ztoxy, n.- or isopropoxy, methylthio, ztylthio, n.- -or isopropylthio, methylsulfinyl, zthyl sulfinyl, methylsulfonyl or zthyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, zthoxycarbonyl, methoxyiminomethyl, zthoxyminomethyl, methoxyminostyl, zthoxyminostyl, methylenedioxy and ztylenedioxy,

HF) unsubstituted or at least monosubstituted by the same or different residues from the groups including fluorine, chlorine, methyl or methyl, phenyl, phenoxy, benzyl and benzyloxy, unsubstituted or at least monosubstituted in the phenyl part by the same or different residues from the groups including fluorine, chlorine, bromine, cyano, methyl, ztyl, n.-or isopropyl, n.-, iso-, sec, or tert, butyl, 60 trifluoromethyl, methoxy, ztoxy, n.- or isopropoxy, difluoromethoxy and trifluoromethoxy.

The above general or preferred values of real radicals! as for target product formulas! (I), and, accordingly, for the initial substances and intermediate products required for their production.

The general or preferred meanings of radicals can be combined with each other in any way you like.

In the event that, for example, methyl ester of o-methoxyimino-o-(2-phenoxy-phenyl)-acetic acid, hydroxylamine hydrochloride and 1,2-dibromethane are used as starting substances, then in the proposed method (a ) the reaction proceeds according to the following reaction scheme:

Vo N.M-oYa x NOI Z a -- «« «-"- --- ! vi-sn,SN.-Ve ro M g M 70 "osn, zosn, o osn, zn Ge) 5 in case, if the starting materials are used, for example,

C-(d-methoxyimino-a-(2-hydroxy-phenyl)-methyl/|-5,6-dihydro-1,4,2-dioxazine and benzyl chloride, then in the proposed method (b) the reaction proceeds as follows reaction scheme: ra on o

M ж СИ-СН.С с сосн, tov Mu --- (Я 2 Е - -к - сосн, с - NOI ! m7 that (o) that (o) in the case, if as INITIAL substances are used, for example, "

3-(-methoxyimino-ou-(2-chloromethyl-phenyl)-methyl/d|-5,6-dihydro-1,4,2-dioxazine and 2-methylphenol, then in the proposed method (c) the reaction proceeds as follows reaction scheme: - si «- sn 7 o (ee) m sn. n-(2-hydroxy-zthoxy)-o-methoxyimino-o-(2-phenoxy-phenyl)-acetamide is used as the starting compound, then in the proposed method reaction (d) proceeds according to the following reaction scheme: » (ee) - (c) o -y a osn --- r. M

T» ts 3 -no to "osn, o Mch ! and (c) (o) tone 9. (F) We need as starting substances for carrying out the proposed method (a) the production of carboxylic acids! determination! formula (II), where Ag, E, b and 7 have preferably or in particular the meaning which, in connection with the description of the proposed compounds of formulas (I), is also indicated as preferred or especially preferred; K means preferably alkyl with 1 to 4 carbon atoms, in particular methyl or zyl.

The original substance of the formulas! (II) lime or it can be obtained by certain methods (see applications 178826, 242081, 382375, 493711).

We use in the proposed method (a) as further reaction substances disubstitution in alkane in the general definition of formula (II). In formula (I), A preferably or in particular has the meaning which, in connection with the description of the proposed compounds of formula (I), is indicated as preferred or especially preferred; X is preferably chlorine, bromine, methylsulfonyloxy, phenylsulfonyloxy or toluenesulfonyloxy.

The starting substance of the formula (III) is a lime chemical! organic syntheses.

Hydroxyaryl compounds as generally defined by formula (IM) are used in the proposed method (b) as reaction agents. In it, A, Ag, and E preferably or in particular have the meanings given in connection with the description of the proposed compounds of the formulas! (And) specify as preferred! or especially preferred.

The starting substances of the formulas: (IM) from the literature are not lime; therefore, as new substances, they represent a further object of invention.

New hydroxyaryl compound formulas! (M) are obtained at the expense of top, that tetrahydropyranyloxy compounds of the general formulas! (them)

SA ur o o - uh ayu ) where

A, Ag and E have the above-mentioned values, are subjected to interaction with an acid, such as, for example, hydrochloric acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, or an acid ion exchanger, if necessary in the presence of a diluent, such as, for example , water, methanol, ztanol or complex acetic acid ester, at a temperature of 0 - 1007"C (see the sample presentation below).

Tetrahydropyranyloxy compounds of the formulas! (ХХ) from literary not lime; therefore, as new substances, they represent the second object of the invention. high school

New tetrahydropyranyloxy compound formulas! (IX) is obtained due to the fact that it is complex (3 formulas (X)

WITH

Ge) o-you ov bo From where --

Ag, E and K have the above-mentioned values, are subjected to interaction with hydroxylamine or its hydrochloride, if necessary in the presence of an acid acceptor, such as, for example, potassium hydroxide, and, if necessary, in the presence of diluents, such as, for example, methanol and water, and the resulting intermediate product in situ is subjected to interaction with dihaloalkanes of the above-mentioned "F general formula! (II), if necessary, in the presence of an acid acceptor, such as, for example, potassium carbonate, at a temperature of 0 - 1002C (see the description of the proposed method (a) and the example presentation below).

The new complex of formulas IX) from the literature is not known; therefore, as new substances, they are "recognized as another object of invention."

A new compound with the formula (X) is obtained due to the fact that it is a compound with tetrahydropyranyloxy-phenyl-acetic acid of the general formula! (XI)

SA o o o d (XI)

Сг», where сАг and К have a higher value, are subjected to derivatization by ordinary methods (see the presentation of the example below). - A new complex of tetrahydropyranyloxy-phenyl-acetic acid of the general formula! (XI) from the literature of 20 not limes; therefore, as new substances, they are considered an additional object of the invention.

New complex zfir! tetrahydropyranyloxy-phenyl-acetic acid general formulas! (XI) receive at the expense of what is complicated! hydroxyphenylacetic acid of general formulas! (ХИЙ) о in notes od

F! where

Ag and K have the above values, are subjected to interaction with dihydropyran, if necessary in the presence of a catalyst, such as, for example, p-toluenesulfonic acid, and, if necessary, in the presence of a diluent, such as, for example, tetrahydrofuran, at a temperature of 0 - 1007 (see below 60 presentation examples).

Derivatives of substances of formula (XII) are lime chemicals! organic syntheses

Used in the proposed method (b) as further starting substances of the compound in the general definition of formula (M). In the formula (M), 7 preferably or in particular has the meaning that it has in connection with the description of the compounds of the formula! (I) instructions as preferred! or especially preferred; X is preferably chlorine, bromine, methylsulfonyloxy, phenylsulfonyloxy or toluenesulfonyloxy.

Reaction agencies of formulas! (M) are lime chemical! organic syntheses.

ХХХХХХХ

In the proposed method (c) of obtaining halogen methyl compounds in the general definition as starting substances! by the formula (MI), in which A, Ag and E have preferably or in particular the meanings that are also in connection with the description of the proposed compounds of the formulas! (And) instructions! as preferred or especially preferred; X! means preferably fluorine, chlorine, bromine or iodine, especially preferably chlorine or bromine.

The original substance of the formula! (MI) from literature! don't lime!; therefore, as a new substance, they are considered a further object of the invention.

New halogen methyl compounds of formulas! (MI) are obtained due to the fact that methyl compounds of general formulas! (XII) h-o no tue v-y A ho o where

A, Ag and E have the above-mentioned values, are subjected to interaction with a halogenation agent, such as, for example, n.-bromo- or n.-chloro-succinimide, if necessary in the presence of a catalyst, such as, for example, azoisobutyronitrile, and, if necessary, in the presence of a diluent, such as, for example, tetrachloromethane, at a temperature of 0 - 1507C (see below for an example).

Methylene compounds of the formula IHIIII) from the literature are not known as preliminary products!; therefore, as new substances, they are considered an additional object of the invention.

Newer methylene compounds of the formula (XIII) are obtained due to the fact that the compound of the compound of the general formula Ha (ХИМ) about (8)

AH no AoE7 ov a « where «-

Ag, E and K have the above-mentioned values, are subjected to sequential interaction with hydroxylamine or its hydrochloride, if necessary, in the presence of an acid acceptor, such as, for example, potassium hydroxide, and, if necessary, in the presence of a diluent, such as, for example , with methanol, and with a disubstituted alkane of the above-mentioned general formula (II), if necessary, in the presence of an acid acceptor, such as, for example, potassium carbonate, at a temperature of 0 - 1507 (see below "presentation of the example).

Preliminary product! formulas! (CHEM) lime or they can be obtained by certain methods (see applications EP 386561, 498188, examples are presented below)). "

Used in the proposed method (c) as starting substances are compounds generally defined by the formula (MI), in which O, and 7 preferably or in particular have the meaning that, in connection with the description of the proposed compounds of the formulas (I), is indicated as preferable or especially in preference. » The original substance of the formula! (MINE) are lime chemical! organic syntheses.

In the proposed method (d), hydroxyalkoxyamide is used as a starting material! in the general definition by the formula (MI), in which A, Ag, E, Z and 7 preferably or in particular have the meaning that is in connection with the description of the proposed compounds of the formulas! (And) specify as preferred! or about special preferences.

The original substance of the formulas! (MI) from literature! don't lime!; therefore, they, as new substances, are recognized as another object of the invention. -oUu 70 New hydroxyalkoxyamide! formulas (MI) are obtained due to the fact that the derivation of general formulas (XM) (9) t» got you where

Ag, E, b and 7 have the above-mentioned meanings, and o U means halogen, hydroxy or alkoxy, are subjected to interaction with hydroxylamines of the general formula (HMI)

NhM-O-A-OH (HMI) 6o where

A has the above meaning, if necessary, in the presence of an acid acceptor, such as, for example, trisethylamine, pyridine, or 4-dimethylaminopyridine, and, if necessary, in the presence of a diluent, such as, for example, methylene chloride, toluene, or tetrahydrofuran , at a temperature of 0 - 15076 (see applications ER 178826, 242081, 493711). 65 Derivative formulas are required as preliminary products! (HM) lime or it can be obtained by lime methods (see U. Spet. Vos. RegkKiIp Tgapv. I 1987, 2829 - 2823).

We offer a way! (a), (6) and (c) are carried out preferably in the presence of an acid acceptor!. As acid acceptors! adventure! all organic or inorganic bases. К ним принадлежат, например, гидридьї щелочноземельньїх металлов или щелочньїх металлов, гидроокиси щелочноземельньїх металлов или щелочньх металлов, амидь щелочноземельньх металлов или щелочньх металлов, алкоголять щелочноземельньїх металлов или щелочньїх металлов, ацетатьї щелочноземельньхх металлов или щелочньх металлов, карбонатьї щелочноземельньх металлов или щелочньх металлов или гидрокарбонать щелочноземельньїх metals or alkali metals, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium tylate, tert, potassium butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, /o sodium acetate, potassium acetate, calcium acetate, ammonium acetate , sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate or ammonium carbonate, as well as tert, amine, such as, for example, trimethylamine, tristhylamine, tributylamine, M,M-dimethylaniline, M,M-dimethyl-benzylamine, pyridine, T-methylpiperidine,

M,M-dimethylaminopyridine, diazabicyclooctane, diazabicyclononene or diazabicycloundecene.

As a diluent for carrying out the proposed methods (a), (b) and (c), water and organic solvents are used. These include, in particular, aliphatic, alicyclic or aromatic, if necessary halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, simple petroleum sulfur, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride, simple sulfur), such as, for example, disethyl sulfur, diisopropyl sulfur, dioxane, tetrahydrofuran, or ethylene glycol-dimethyl or 2-ethylene glycol-disethyl sulfur!; ketones, such as, for example, acetone, butanone or methyl isobutyl ketone; nitriles such as, for example, acetonitrile, propionitrile or benzonitrile; amide), such as, for example,

M,M-dimethylformamide, M,M-dimethylacetamide, M-methylformanilide, M-methyl pyrrole idone or triamide hexamethylphosphoric acid!; complex esters, such as, for example, methyl ester complex with acetic acid or zyl ester complex with acetic acid; sulfoxides, such as, for example, dimethyl sulfoxide, with alcohol! such as, for example, methanol, zethanol, n,- or isopropanol, simple ethylene glycol-monomethyl sulfur, simple ethylene glycol-monomethyl sulfur, simple disethylene glycol-monomethyl sulfur, simple i) disethylene glycol-monomethyl sulfur, their mixtures with water or pure water.

The proposed method (d) is preferably carried out in the presence of means of dehydration. At the same time, as a means of dehydration, in particular, adventure! ordinary water-removing chemicals, in particular "Ezo anhydride! acids such as, for example, phosphoric anhydride.

As a diluent for carrying out the proposed methods (d), generally accepted inert organic solvents are used. These include, in particular, aliphatic, alicyclic, or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, simple petroleum sulfur, hexane, cyclohexane, dichloromethane, so c5 chloroform or carbon tetrachloride, simple sulfur, such as, for example, diethyl sulfur, diisopropyl sulfur, dioxane, tetrahydrofuran or ethylene glycol-dimethyl or ethylene glycol-disethyl sulfur; ketones such as, for example, acetone, butanone or methyl isobutyl ketone; nitriles such as, for example, acetonitrile, propionitrile or benzonitrile; amide), such as, for example,

M,M-dimethylformamide, M,M-dimethylacetamide, M-methylformanilide, M-methylpyrrolidone or triamide "hexamethylphosphoric acid); complex acetic acid), such as, for example, acetic methyl acetic acid (2-3 s acid or acetic acid complex zytyl acetic acid!); sulfoxide, such as, for example, dimethyl sulfoxide.

The reaction temperature when carrying out the proposed methods (a) - (d) can vary widely; limits They generally work at a temperature of -20 - - 200"C, preferably at a temperature of 0 - 15076.

To carry out the proposed method (a) per mole of carboxylic acid derivative! formula (II) generally uses 1 - 5 mol, preferably 1.0 - 2.5 mol, of hydroxylamine or its hydrogen halide salt and 1 - 1 mol, preferably 1.0 - 5.0 mol, of a disubstituted alkane of formula (PI).

To carry out the proposed method (b) per tmol of the hydroxylaryl compound of the formula! (IM) generally use 0.5 - 2.0 mol, preferably 0.9 - 1.2 mol, of compounds of formula (M). - To carry out the proposed method (c) on thymol halogenated compounds of the formulas! (MI) generally 5 p Mspolzuyut 1 - zmol, preferably 1.5 - zmol, compounds of formulas! (E). - To carry out the proposed method (g) per Tmol of hydroxyalkyloxyamide of the formulas! (MI) generally use 1 - 5 mol, preferably 1.5 - 4 mol, means of dehydration.

Reactions, processing of reaction mixtures and isolation of target products are carried out by known techniques (see below for an example presentation). 5B The proposed active substances have a strong microbicidal effect and can be used to combat unwanted microorganisms. Therefore, active substances are useful as means (F, plant protection, in particular, fungicide. Fungicidal means for plant protection are used to combat plasmodiophoromycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidomycetes, and deuteromycetes. 60 In the following, several examples are given causative agents of fungal diseases belonging to the above-mentioned families,

See Ruyisht, such as, for example, RuUSHISHt otyt,

See Rpuiorpipoga, such as, for example, Rpuiorpiyoga Ipteviapv,

See Rzeydoregopozroga, such as, for example, Rzeydoregopozroga drink! or Rzeidoregopozroga sirepve, 65 See Riaztoraga, such as, for example, Riaztoraga mISHsoia,

See Regopogzrog, such as, for example, Regopozroga rivi or Regopozroga Bgazvi-saye,

See Eguzirpe, such as, for example, Eguzirpe dgatipov,

See 5ZriaegoiPpesa, such as, for example, Zrpiaegoipesa cIdipea,

See Rodozrnaega, such as, for example, Rodozrpayega Ieisoigisna,

See Mepishgia, such as, for example, Mepishgia Ipaedzai5,

See Rugeporgoga, such as, for example, Rugepornoga (eges or Rugeporpoga dgatipea (conidial form:

Ogespziega, synonym: NeiItipipozrogiit),

Species of SospiIorois5, such as, for example, SospiIorois zaymiz (conidial form: YuOgespzieega, synonym:

Neitipiyozrogiit), 70 Vidy Ogotusez, such as, for example, Ogotusez arrepaiIsshayiv,

See Rissippa, such as, for example, Rissippa hesopaca,

See TPeya, such as, for example, PIeya sagiev,

Forms of OzNiado, such as, for example, OzNiado pida or OzNiado amepae,

See Reissiagia, such as, for example, Reissiagia zazakkii,

See Rugisciagia, such as, for example, Rugisciagia ogugaye,

See Ryzagisht, such as, for example, Ryzagisht sitogyt,

See Voiguis, such as, for example, Voiguis sipegea,

See Zeryogia, such as, for example, Zeryuogia podogyt,

See I eriozriaegia, such as, for example, I eriozrpaiegia podogyt,

See Segsozrog, such as, for example, Segsozrog sapezsepv,

See AGegpagia, such as AKegpagia Bgazvisae,

See RzeydosegsozrogeiIa, such as, for example, RzeydosegsozrogeiIa pegroihispo!1-dev.

The good tolerance of active substances by plants in concentrations necessary for the fight against plant diseases allows the processing of above-ground parts of plants, planting and sowing materials, and soils. with

At the same time, the proposed active substance can be used especially successfully for the fight against diseases in the field of fruit growing and fruit growing, such as, for example, with the causative agents of RPuiorpioga, or for the fight against diseases of bread cereals, for example, for fighting! with pathogens of Rugeporrog.

In addition, the proposed active substances have a good effect, for example, in the fight against the pathogens of Egisurpe dgatipiz, SospPoroiShe zaimiv, I erio-zrpaega podogyt, RzeiydosegsozrogheiPa "g zo Pegroihispoides and with species of Rhizagit on bread cereals, with pathogens of Rugisgia ogulae and ReiSsshagia zazaki! on rice They also have a wide in-vitro effect. --

Active substances can be converted into standard preparations, depending on their physical and/or chemical properties, for example, solutions, emulsions, suspensions, powders, stumps, pastes, granules, aerosols, polymer microcapsules and shells for seed material. In addition, they can be a preparation for extremely fine distribution in the form of cold and warm fog. "Mr

This preparation is obtained by certain methods, for example, by mixing the active substance with fillers, for example, with liquid solvents, pressurized liquefied gases and/or solid carriers, if necessary with the use of surface-active substances, for example, emulsifiers and/or dispersants and/or foaming agents When using water as a filler, you can also use an organic solvent as an auxiliary agent. As an organic solvent, the following are mainly used: aromatic hydrocarbons, such as, for example, xylene, toluene, or alkyl naphthalene, chlorinated aromatic and aliphatic hydrocarbons, for example, chlorobenzenes, chloroacetylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffin , for example, petroleum fractions, alcohol, such as butanol or glycol, as well as their simple properties

M complex solvents, ketones, such as acetone, methyl acetyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, as well as water. Liquefied gaseous fillers or carriers should be understood as liquids that are gaseous at ambient temperature and atmospheric pressure, for example, working gases! for aerosols, such as, for example, halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.

As solid carriers, for example, natural mineral flour, such as kaolin, alumina, talc, chalk, quartz, attapulgite, montporillonite, or diatomaceous earth, and synthetic mineral flour, such as highly dispersed silicic acid, aluminum oxide and silicates As solid carriers for granulates, for example, grinding and fractionation of natural stone rocks, such as calcite, marble, pumice, sepiolite, dolomite, synthetic inorganic and organic

B Flour, as well as organic materials, such as sawdust, coconut husks, corn cobs! and stalks of tobacco.

F) As an emulsifier and/or foaming agent, for example, nonionic and anionic emulsifiers are used, such as complex polyoxyethylene resin of fatty acids, simple polyoxyethylene resin! fatty alcohols, for example, acyl-aryl-polyglycolic acid, alkyl sulfonation, alkyl sulfate, 60 aryl sulfonation, and soluble protein hydrolyzate. As a dispersant, for example, spent ligninsulfite alkali and methyl cellulose are used.

The preparation! may also contain a binder, such as, for example, carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymer, such as, for example, gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin and b5 synthetic phospholipids. Other additives can be mineral and vegetable oils.

In addition, the preparation! may also contain dyes, such as, for example, inorganic pigments, for example,

iron oxide, titanium oxide, ferrocyanine blue, and organic dyes, such as alizarin, azo- and methylphthalocyanine dyes, and nutritional trace elements, such as salts of iron, manganese, boron, copper, cobalt, and tin.

The drug! usually contains 0.1 - 95 wt. 95% of the active substance, preferably 0.5 - 9% by weight. 905.

The proposed active substances can be used as such or in the form of their preparations, as well as in the form of a mixture with known fungicides, bactericides, acaricides, nematocides or insecticides, for example, in order to expand the spectrum of action of active substances or to prevent infestation. In many cases, a synergetic effect is obtained, i.e., the activity of the mixture exceeds the activity of the individual 7/0 components.

The following compounds are particularly advantageous for combining with the proposed active substances:

Fungicide!: 2-aminobutane; 2-anilino-4-methyl-b6-cyclopropyl-pyrimidine; 2,6'-dibromo-2-methyl-4-trifluoromethoxy-4"-trifluoro-methyl-1,3-thiazoly-5-carboxanilide; 2,6-dichloro-M-(4-trifluoromethylbenzyl)benzamide; (E) -2-Methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide; 8-hydroxyquinoline sulfate; methyl-(E)-2-2-(6--2-dianophenoxy)pyrimidin-4-yloxy|phenyl)-Z -methoxyacrylate; methyl-(E)-methoxyimino(alpha-(o-tolyloxy)-o-tolyl|iacetate; 2-phenylphenol (ORP), aldimorph, ampropylphos, anilazine, azazonazole, benalaxyl, benodanil, benomyl, binapacryl, bi- phenyl, bitertanol, blasticidin-5, bromuzonazoles, bupyrimat, butiobate), calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate, chloroneb, chloropicrin, chlorothalinil, clozolinate, zufraneb, cymoxanil, cypro-zonazoles, ciprofuram, dichlorofene, diclobutrazol, diclofluanid, diclomesin, dicloran, distofencarb, difenoconazole, dimethyrimol, dimethomorph, dinisonazole, dinocap, diphenylamine, dipyrithione, dithalymphos, dithianone, dodin, drazoxolone, zdifenfos, zpoxyzonazole, tyrimol, ztridiazole, fenarimol, with fenbutonazoli, fenfur am, fenitropan, fenpiclonil, fenpropidine, fenpropimorph, fentinacetate,, fentinhydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromid, fluhinzonazoli, i) flusilazoli, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, phthalide, fuberidazole, furalaxil, furmecyclox , guazatiny, hexachlorobenzene, hexazonazole, hymexazole, imizalyl, imibenzonazole, iminoctadine, iprobenphos (IPR), iprodione, isoprothiolane, kazugamycin, preparations of copper, such as copper hydroxide, copper naphthenate, copper chloride, copper sulfate, copper oxide, copper oxide and Bordeaux mixture, mozn-copper, manzozeb, maneb, mepanipyrim, mepronil, metalaxyl, metzonazole, - metasulfocarb, metfuroxam, metiram, metsulfovax, myclobutanil, nickel dimethyldithiocarbamate, "- nitrotal-isopropyl, nuarimol, ofuratsi, oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penzonazole, pencizuron, fosdifen, pimaricin, piperaline, polyoxin, probenazole, prochloratz, procymidon, propamocarb, so

From propizonazol, propineb, pyrazophos, pyrifenox, pyrimethanil, pyrochilon, hintosene (RSMV), sulfur and sulfur preparations, tebuconazole, tecloftalam, tecnazen, tetrazonazole, thiabendazole, thithiophene, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon , triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflumizol, triforin, tritizonazol, validamycin A, vinclozolin, zineb, ziram.

Bactericide!: Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamicin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other preparations of copper. ;" Insecticide, acaricide, nematicide!: abamectin, acephate, acrinathrin, alanicarb, aldicarb, alphamethrin, amitraz, avermectin, A7 60541, azadirachtin, azinphos A, azinphos M, azocyclotin, VasShiv Ipygipdiepv, their 4-bromo-2-(4-chlorophenyl) )-1-(ztoxymethyl)-5-"trifluoromethyl)-1H-pyrrolyl-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betaciluthrin, bifenthrin, VRMS, brofenprox, bromophos A, bufencarb, so buprofezin, butocarboxin, butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion, - carbosulfan, kartap, chlorztokarb, chlorztoxufos, chlorztoxifos, chlorfenvinphos, chlorfluazuron, 5r Chlormefos, M-((b-chloro-Z-pyridinyl)-methyl/)-M'-cyano-M- methyl ztanimidamide, chlorpyrifos, chlorpyrifos M, - cis-resmethrin, clocitrin, clofenthesin, cyanophos, cycloprothrin, cyfluthrin, cygalothrin, cyhexatin, i» cypermethrin, cyromazine, deltamethrin, demeton M, demeton 5, demeton-5-methyl, diafentiuron, diazinon, dichlofenthion, dichlorphos, diclifos, dicrotophos, disthion, diflubenzuron, dimethoate, dimethylvinphos, diox athion, disulfoton, zdifenfos, ozmamectin, zsfenvalerate, zthiofencarb, ozthion, ztofenprox, ov Ztoprophos, ztofenprox, ztrimfos, phenaminophos, phenazakhin, fenbutatin oxide, fenitrothion, phenobucarb, phenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpiroximad, fenthion, fenvalerati, fipronil,

F) fluazinam, fluazuron, flucycloxuron, flucitrinate, flufenoxuron, flufenprox, fluvalinate, fonofos, ka formotion, fostiazate, fubfenprox, furatiocarb, HSN, heptenofos, hexaflumuron, hexityazox, imidacloprid, iprobenfos, isazofos, isofenfos, isoprocarb, isoxathion, ivemectin , lambda-cyhalothrin, bo lufenuron, malathion, mecarbam, mervinphos, mesulfenphos, metaldehyde, metacriphos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, mylbemectin, monocrotophos, moxidectin, naled, MC 184, nitenpyram, ometoate, oxamyl, oxydemeton M, oxydeprophos, parathion A, parathion M, permethrin, pentoate, phorate, phosalon, phosmet, phosphamdone, foxim, pirimicarb, pirimifos M, pirimifos A, profenofos, profenofos, promecarb, propafos, propoxur, protiofos, protoate, pymetrozin, pyrachlofos, pyraclofos, 65 pyraclofos, pyradfenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxyfen, quinalphos, salithion, sebufos, silaftofen, sulfotep, sulprofos, tebufenozide), tebufenpyrad, tebupyrimphos,

teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, tiafenox, thiodicarb, thiofanox, thiometon, thionazine, thuringiensin, tralometrin, triaraten, triazophos, triazuron, trichlorfon, triflumuron, trimetacarb, vamidothion, KhMS, xylylcarb, U! 5301/5302, Zetamethrin.

The proposed active substances can also be found in preparations in a mixture with other known active substances, such as herbicides, as well as with fertilizers and plant growth regulators.

Active substances can be used as such, in the form of their preparations or working forms obtained from them, such as, for example, ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, means for dusting and granulation. They are used by known methods, for example, by pouring, spraying, spraying, spreading, foaming, applying with a brush, etc. In addition, it is possible to apply the active substance by the method of ensuring extremely fine distribution or injecting the agent or the active substance itself into the soil. Processing of seed material of useful plants is also possible.

When processing parts of useful plants, the concentration of the active substance in the drugs used /5 can vary widely.

It generally amounts to 1 - 0.0001 weight. 95, preferably 0.5 - 0.001 wt. 9b.

When processing seed material, 0.001 - 50 g of active substance per kg of seed material is generally used, preferably 0.01 - 10 g.

When treating the soil at the place of application of the active substance, concentrations from 0.00001 to 20 O.Twes are required. 96, preferably 0.0001 to 0.02 wt. 90.

Examples of obtaining compounds of formula (I)

Example 1 lo ; 25 o'clock (8) Sun, Sun, Sun From 30

And KK a! - with - s

To 1.8 g (25 mmol) of hydroxylamine hydrochloride in 20 ml of methanol at 207"C slowly add a solution of 3.3 g

From 8695 potassium hydroxide in 20 ml of methanol. Then 4.0 g (12.8 mmol) of complex methyl ester o-methoxyimino-o-(2-(2-methyl-phenoxy-methyl)-phenyl|-acetic acid is added in portions, after which the reaction mixture is stirred at 407"C until the end of the reaction, determined by thin-layer chromatography. After that, first 1.7g (12.8mmol) of potassium carbonate is added to the reaction mixture, and then 10.8g (59mmol) of 1,2-dibromostane. The mixture is stirred for 12 hours at 65-7C, then cooled to 207C and filtered. 40 The filtrate is concentrated in a vacuum obtained with the help of a water jet pump, and the residue is purified by chromatography on a column containing silica gel (solvent: toluene and acetone in a volume ratio of 9:1). : » They get 1.4g (3390 theories)

3-(α-Methoxyimino-o-(2-(2-methyl-phenoxy-methyl)-phenyl|-methyl)-5,6-dihydro-1,4,3-dioxazine.

Refractive index pr? - 1.5705. Similarly to example 1, as well as in accordance with the general description of the proposed methods, it is possible to obtain, for example, the compound of formula (1) shown in the following table 1. (ee) 7 M-or - ry ( - 7"H-NMR-spectrum! of absorptions in SOCIz with tetramethylsilane as an internal standard. Chemical

T" displacements, as a rule, are given by values of 5.

Table 1: examples of compounds of formula (I) example 7 b Ag EA A / physical data mer -Щ

Psalm 5:15; 7.0-7.68 h/mile. 60 3 But the day Fr. di bnn, "HIRE: 2.23; 2.25, 3.98, 4.1. rf ment la sno 4.52; 705-7.55 h/mile. not b5 example 7 b Ag E A physical dannye shnnnnnntnshtshtshtshlshlzhFyn nn A A A A A a OO OO A a OO O OO LEAD OO ? 4 in; and sn,sn,

And She la snuU-sn-su

OK

M.

WITH

70 o'clock in the morning

M. 8 b o) yo snsNn

And 1 snyu-sNesi g b

M. 5 7 o'clock, night

I s s pri- (8) mer 7 b At E Dd / physical data -Me p И 8 o snen snyu-snes she - "- sn, tr cm 1 "--

Co

And about sleep-snes dreams, so "7 o, where - not so "in "

Io (9) snyun te snuU-sNnes shi -o s - in! - "» not M p m.

ChK" (ee) - shu 20 "z" ko 60 65 example 7 b Ag E A / physical data -M - 5 6 ("6 ; 6 Ж Ж. 6Ж Ж ( 6 6----2-2 -2- :.Д097:й34.373- 3: 052И0Щ0337333331-

AND! o сН.сН, t. pya. 1387S

Mokh sno " y ro z - 4 M

II mV,

I2 c) sN.sn, t. pl. 6520 y: stvom she

She from Z-

M. -- M

GI m

From (0) ry CHCH, (amorphous) c) sne IN-NMR: (SOS) 5 5 - 3.75 (538) rain and 4 6) sNen, t.p. 707С " ron shi

As. se example 7 s Ag E d / Physical data (o) - What chinchilla shinnyshshnshshi 15 o sn.sn, oil snnes s 7 r-YAMe (SОСО) 5 - 3.80 (53) - not K -

Sh. "5 h- 16 50, sun, re sun.sun,

I: Me: -m- (ee) la snom d t "I

Code

I7 vsO -osn,- ra sn.sn,

T Z) sn., O-mes "

Ш- and х - си - IV base. rya snen amorphous "» ! sno-mess 7 NEM. 1.55, 3.97, 4.16; 4.48, 5.03, 7.08- 15 gas 7.51 chu/mile, s" (ee) shk tsu 5

I" (F. ko 6o 65 pri- i i b Ag EA A / physical data 19 ne -osn,- re СН,СН, warm 297 mo dis yen, 20 sn -osn, tolerable (amorphous) to z? stos 77 anoyamr. 2.24; 2.28; 3.99, 4.15; 4.46; 4.98; 6.62- 7.59 chumil. sn with 271 not -OsN.- snen ce | o snyumes S she -

SI

22 -osn, ra SN.SN, 7. la. IS si s (8) example 7 s Ag E A physical data - change A a In A nn i o i i " 23 Ve "osn, sn.sn,

Od en y

She «- 24 i-s3n, O -osn,- tlo sen, so snu, - 25 snUysn-sn, osn, snom sn,sn,

HC novel « 70 20 si -osn, ra sn.sn, Z toro ron ;z" 217 si -osn.,- ra sn.sn, snu-mes ve si (og) - example 7 b Ag E A physical today - 50 -Me

Im 28 o'clock snomes77 0 sNSN, 3 - not 29 (8) -h snom-s77 00 bNsn,

GF) I r with No

Mko 30 6) ra SNAN, oil g snumeso 60

With b5 mayor 7 b Ag E A physical data

SHA nn On a o sn.sn one 32 Mo o. y sNen, named Teonyala sne

Щ сн.сН from Mody zone, reben sn-la snyu-meos not 34 ne m o oi nen, from X byu sn-- la snumess 35 m o oy stsn,

СХ be snA- la snyuess

SI with example 7 Ge! Ag E A physical data Ge) -Me 1 (PR ОСы .ТЧЧТЧТЭТ s.en 36 si mo Ge t sn,

Xia Tony- sno - y snen - 37 M o dy 2-7

DY b snyvv syu i si sn,sn so sh s M o Zh 2, -. mes bot people -

I slept on the 39th of the month of the year of Tonyaro snyumss

VG

7 sten -v sno Mo o shcha sn, s z De - tsni- LO snyunyaso;" sleep

ChK" (og) - - 50 t" (F, ko 60 b5 example 7 b At E A physical data -Mo t OO ' t. 41 sno m o. l sNnen, z ne b i s- la snyuess 42 Mo o. il nen,

S e-- sn/- o. snyu-meso 43 Mo oh, it sn, g Sam Tsnlo snyumess !

CHE - y y sn.esn with mo o che 2-2 ve Sam Tony- LO snyumess sn, 7 sn.sn 45 Mo Ou o ra 2 2

KH r tlia la sleep not with 7 and annie pi A fiziskie d; Ho) mer y a Ag E 2 2 o (S6«S E Y H IO.- E snen 46 cho o Y r zn,

TO yam Tsnyla snyu-ness her 7 snen "- 47 OM n Ge) m r 2272 ! F Uzhyu tvnilo snyuo-m-ss and sn.sn (so) 48 si Well o. sn omes/7 2-p; bod t dya i ra sn.sn « 2 2

S Sho a a snyu-mes with 40 Mt With sn.sn, 50 and obnA-- sleep : " p DIT -

M

Sg" with t E o At E A physical data - yo and i o sn, - 70 Yezhi sniasno SN NYAM (SOS, 5): 2.26 (ZNU; 3.96 ZNU; 41-42 th" yo (2H); 4.4-4.5 (2H): 5.204 (2H); 7.0-8.0 (8NI) h/mill. 52 we snyu-sness sn., sn, iF) syu ko 53 because nn syuosnes7 SNSN,

UK

D9)

Wed b5 example 2 b Ag E A physical data -M shi for sn, -osNu (vi snonschshi Snn, "N-YAMRSSY,, ВХ 20 z y (ZNU; 3.98 (ZNU; 4.1-4, 2 (2 E (OH); 4.4-4.5 OH); 4.97 (2H); 6.4-7.4 (7H) h/ml. 55 sn (c) stsn, "H-NMR - (SOS, 5U: 2.25 and stuo-mes 27 Z -s«m.O-sH,. 1 and (H); 4.0 (3H); 4.1-42

KU U: (2H); 4.4-4.5 (2H); 5.176 (2Nu; 7.114-7.131 (IN); 7.44-7.45 (IN); 7.4-8.0 (4Н) h/mil. b Ag E A physical data pana ma aa cha a a a aa Y a a i i i i o o o OO Nu o nu se 57 si -0- y сНСН, (amorphous) снюос H-NMR:(СОСИ,) Ge) 5 - 3.80 (5.3N) Ge

And "I

And from M. in A «- 58 sn -СН,о- and СНСН, t. pl. 1427

Wed, Sep 7 - . (ee) 539 sn, -СН,ЧО- 7 snNewesn, oil ns 60 -0- t. pl. 106C gron;

ZHA si - s :z» pritm gYa b Ag E A physical data in NNNNTN-NN--- In soda - cen snyuness stsnu t (ee) ZHA - SM . - 50 oil "from" 62 sn, -0- t сНСН, , g of snow H-NMR: (SOCI,) in 5 3.80 (5 N)

M

1 m. 63 not sn -сСН.,0- 12370 (Ф) with С with 2 years of snyuness СН,СН, t. pl. ko ba -oSN.- 17520 bo sn, 2 lo snotessi SN,SN, t. pya. and b5 example 2 b Ag E A physical data -M2 nan nanni aaShazhayaaalayazhZHYUyaaHnnnchaaanannnnnnnnnnnnnn o - - sNen, t. pl. 1199С 65 С оси, Ти Z снюнес с 7

What v3s - - SN.SYA, t. pl. then 1 - (amorphous) I-NMR: 7 hosp snyunnss sne, 3.98; 4.15, 4.47, 4.98, 6.80;

KH 7.55 chumil. see (amorphous) "H-NMR: 2.27; - Ho z 68 ne -os snyuness snesn, 3.97; 4.14; 4.47; 4.96; ne 6.18-7.53 h/ml. ' and N. (amorphous) H-NMR; 3.95, 69 Osn, "Osn, snyuness sn, 4.15; 4.48, 5.07; 6.92-7.54

FI h/mill.

I mer E A physical data sch mer 7 (4. Ag o -Mo - t.pl.131C 70 Vg -OSN,- ro snyulnss7 sn.sn,

С и - п.д- дл СНеСН, t. pl. 9520

Fe rony - - - - Ssn.sNn. oil from XX; and pe dl СНоСН, t. pl. 11920 73 not -0- ; snyumeos 27 and 5 « sNn.sn, oil 7 neo t: that plot o) s | Her in it t" (og) - - 50 "z" (F, ko 60 b5 example 7 b Ag E A physical data a 2020202 (OLO O " "(p t "E X" S I "t 7U -0- s.s.n. oil stood h o 1 to se 5 76 -0- lo sne, (amorphous) kerosene and "7 -0- s.s.sn. oil "H-NMR(SOCI) nt snyumess 27 5 - 3.80 (5, ZN)

ZHA

Osn, 78 -CH,5- snen

M m 5 s at: ; A / physical data o measure i o Ag E Czech data 000010 t "o "o 2 20 060606 -5C11,- snsn 79 No? dream

M

Zh M o SI -SN.,5- r snen, sn.,Oo-m-S s - » ro mov -56N.- snisn liu 81 si s n la sno What " s m z . | X i" M. in 82 there is also sn.sn, sno М so M. 7v - - 50 "g" (F. ko bo b5 mer Y, A izicheskie dannie mer 7 b Ag E f -Me 9 83 - schu dreams

M sho) mo to -0- sn,sn

M

(1

M. in that -o- snisn, oil"H-NMR(SOSI,) sn,

CODE

75 s Ag E A physical data pri- 7 mer - sch -Me u snen, Z pl. 1287С o. sleep,O-mes o paron sleep of speech, « «- ry snisn,maslo "N-NMR(SOSI) - 87 Teh -0- la sum 5 - 3.80 (5311) so sleeps «!

To n Fri sne, then 88 si si -0- sno From s 7 h to

M. in g" (ee) - - 50 s"

Ф) име) б5 example и а Аг Е А physical data -M ssypaistiniiTlplsSBchTTiyuiiitchnnshshsh

Phi ro

Her and

M.

And what 90 -0- ro sht sNnen, sn,chO-m-s

S. V

DI

M

"in 91 -0- pl" sNSN, t. pl. 7022 and his: a

M. 5 92 n.so -0. shu sNen, t. pl. 750-736 years old p

R ha Ge)

M. 5 "I example 7 with Ag E A physical lannye "-- -M2 жншннннншяняняняняняжтннннннннннннннннннннннннннннннннннннынныннынныnederededededed 93 osn -0- snsn, morpho and with snyuchmess 77 known (СоС 5 - 3.85 (53Н) со

M

on "

Oil code 94 OsNE, -0- ro and snen, сНнУО-мес 5 - 3.55 (5, ЗН)

С, с С щ с 75 95 -8- снен з» Vg o snyutno s o pl, 13290 ше

M. ve and nen 96 si -0- dl sNSN, so vo snuyeness - I M schi SD "g" (F) ko) bo b5 pri- Y I

ShK 2 o Ag E A physical data 97 not -0- background sNnyuN

AND

M. b v. 98 r -0- dya snesn, oil "H-NMR (SOSI,) chn m sune she 5 - 3.80 (5,3Н)

IN

WITH

99 r -0- dya snen, oil mn snyunss 0707 8-380(5.3Н)

CC o sn, s (5) pri- . And physical data mayor 7 GO Ag E 2 KS EZHE « Z E J te lot tamorphyu 1100 оснсн, amor

Ioo men sno 000007 "H-NMR(SVSI)) "

U b - 3.80 (5, ZN) - - si -- (ge) o- snesn « 101 mm la snuness she

UA

E "- с -0- sht sne, amorphous xz" 102 mn ro sno 5 - 3.80 (in, ЗН)

UA g" (ee) sn, - - 50

Thursday"

Ф) ho bo b5 mer and 9 Ag E A physical data that that. sn.sn, amorphous mm stumes sha rf

UA t 1IN-NMR (SOSI;) 6 - 3.80 (5.3Н)

SI

15 that 7 o'clock sleeps, but 20

E s 25 (o) mo a At E A physical data mer y 1 a 00000000 -- t tt t lovyh -0- di snen, zmorphno si yi "g

Zo "b sn, O-Mes zn-YAMe-: z

I | To i y 5 - 3.80 (5, ZN) "- y "- (ee) h sn with v. lo snen, amorphous 106 mm sumo "'H-NMR(SOSI) " ! 5 - 3.80 (5, ZN)

UA - s;" at 45 s» si (ee) - - 50 s» (F) ko bo b5 example /y o Ag E A / physical data -M? 107 r -op- pl sNyun, takh t M snu ul o and oil 108 ra -0- to svsn, mom sn,O-chgs H-yaMR(SOSI,) and UA la | t b 7 3.59 (v, zni rya and se, pri: sch 109 lyu -0- t sNen,

Ve - and M stumesu

UA

« «- «-

In the village

By a -0- sno sn.sn, amorphous - i "H-NMRSOSI) 52380 (5, Z) ag s 2 ;" prime n -o- mm o sn oames snysn, amorphous so-me shki UA and 'H-NMR(SOSI)) - 5 - 3.50 (5, ЗН) ayu sn,

ХТ» сн, и -х -0- lo snen,

Ii M is very amorphous about UA 5 - 3.80 (5, ZN) ime) si 6o si 65 mer 7. (FI. Ag E A physical data a 2 (O0 " LA syu t kht -0- snin " that mm o snyumess 171 butter

And "H-NMR (SOS)

In 5 - 3.80 (5, ЗН) сн, сн, снсн 114 ra -0- stomes 1772 amorphous ro o ! and 6 - 380 (in, ZM) rai, and sleep, sh nen s 115 -0- me ra 2705 nen With sleep

UA

SE. s o mer 7 b Ag E A physical data -2 lush A A A A Y A a A I I i I i I I i i i i « schi -0- snesn u. nH-NMR (SOCI.) - with sn, 6 - 3.80 (5, ЗН) с « 117 -0- snsn with v ron ? -y h u i" si SI g" (o) - - 50

Thursday"

F) ko bo b5

Vr.- 7 b Ag E A physical data

Mg. ra "H-NMR (SOCI,) - 3.80 (5, ZN) and ) 119 -6- snsn

And ra 5 - 3.80 (5, ZN) si pri: physical data sya mer 7 b Ag E And what Go) -Me кжшшшшШшшшшшяшяшяшяяяLlzhdЕЖЯЯЯОЦСХЮОИЯЯЯЯЯЯЯЯЯХЯЮНИНИНИНИВХХХХВТОХВОВЛЗХХХВТОХВОВЛЗХОЮЮХТНВОЮВОЮВВОВ "on- 120 pk. ry 5 - 3.80 (5, ZN) «

SI - "- -o0- sn,sn so mm o snyutess she shre ra ii lo and "sn, "snun ne) 122 -0- ta s schu lo sad :z" HORROR

E g" (ee) - - 50

Thursday"

Ф) ko bo b5 pri- y 2 5 Ag E A physical data m (pet y. tyh 9 123 tlu -0- t sНsН, te -)2 t M sn.,o-m vu ra so

HV 124 la -0- pc sNen,

Ve - " M Z snummesu - ra o example b Ag EA A / physical data a s sch 125 -0- sn.,sn. that tm sno she she (5) ra sn, h- 126 -0- snen mm xue 007 -

I - mA (ge) х и

SI « с - ;» mayor 7 o Ag E A physical data -Mesh sh sny 127 -0- ra m" zm sus shki ro - shu 20

GT» sn, snesn 128 -o- solo snn, tstv a snu t (F; rah yu sn, bo sne, b5 primne 7 ie) Ag E A physical data

Shchi p 129 -0- sn., sn rad ray 277

Mom is heaven

SM

130 r -0- pt sleeps, and Km sleeps amorphously

MIND

IZ not -0- in stos with sn.sn, ry s at o 7 nnne mer ; with Ag E A physical da 20202202 02020200 oo inmorpho 300 osn,isn, amorzhno 132 mm o snujessi shi 1ID-NMR. (SRSI.)

I 5 - 3.85 (5.3H) "I

HA

"- with M Sh cher so -0- snen

ИЗ мн снютнсс 1-77 "

AJ in « and dm - s snen -0- rai 2772 sh Iza mem o snyunyass, !

Yes! three times (ee) M - - 50 s»

F) name) 60 b5 example 7. Ge: Ag E A / physical data 1 p. 135 m -0- сн омест сНасН, amorphous b 5 - 3.85 (5, ЗН) sh- r

I36 -SP,0- pc snsn, 137 ne -sn,od- dl nen, yo de

IZ8 -SN.,op- pt snen, n.s s example 7 b Ag E A physical data about what"

IZO sn -SP,0- snesn with on la snyumess 77 t. sq. m. 14620 with « «- 140 сн, -СН,Од- сНнесн, ro сно «- g)

SNU "I 141 sn, -SN.,O- sht sNnN, ro snomso pes s 142 Go -SN,O- pt sne, no

FI la she. it 75 p 7 s Ag E A physical data (o) 43 -СН.ос- сн.сн. ! And? snyuess 277 - - 144 -sn;o- ol sne, sne "with" m sn -sN.os- sn 5 ? sumo 17 z - (Ф, -СН.,О. сн.,сН ko 146 TS 2 la snunnss that 50 47 in "sn,o- and sn, b5 example 7 s As E A physical data -Mm zhshnntntnlntntntshnntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntntnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn SP.O- sn.sn -SN.,O- snIsn o ns 150 si -sn,f- dl NN, and SN.SN. -snN.,O- 151 si 2 snuo-es s 2772 a n.sn - sN.o- s 2 152 | si z o snyuzhes "4 2 si example 7. o At E A physical data ks sch 153 Sv, ry

SOS -sn., o- lO snu-mess snen, o 154 osn, -SP,Osne snIsn - 2 - 2-7 "-

I55 sh-K -

Fo -sn.o- snIo-mess 0 snen, (ge) « 156 ray

FI -sp,o- With sno-meso sleep, 157 si n 40 . 5 | not

І ZhK snusner-msn, SN, s - navy ma! . si M a 1» example 5 o Ag EA A // physical data -Me (ee) IV nis n A - sn,sn - ne Y Ж snosntnsn ha

M

- 50 159 Wh n in - snesn i" not I Z snosnerchsn, 7 m

Ib0 s and 5

And! A snyu-snestsn, S o a nyny shi ko 161 n - Z snen bo S. H A nn M What

M

162 SI Vg in . snsn not And meh. snyusnenon, 2 b5

2 o Ag E A physical data example n y 163 Vg Ve 5 y - V - spyusirnon, snsn, 70 164 vi y - ІІ sn-s-m-sn. sNeSN ro i hundred-sn and m-sn, sNeSN,

Pav 165 s

Y - sen and sno-sn-s-m-sn, SNN,

ХХ same 3 | IS

Height 166 m---8

ЖА and M snyusnirnen, sn.sn, s and o) about 5 o At E A physical data still 1 pe 904 (St yiv7 ps pe | -

And - ! snyun and not Ukh nt pines 27 - «- 168 SI M--8 - ! snsn p rana snyusninsn, she so h 6 M-8

Sh y y ra residential complex | snesn

M nosno, « 170 SI zh | - - sn.sn, - I, spyusntsn, ; m a 171

Y - tm | walls, 15! A sno-snes-Mosn, t. M (ee) shk shu 20

ЧТ» ко во б5 пример 5 о Аг Е А physical data

AMofe Mie lanno 72 vi

And mess around

M

173 re

Y h M | snisn

ZHA nin M: v.s 7 174 vch snen, and Fi ZHA to the poet 175 ts and 8 ! y snesn, fi va potus s y 7 o Ag e A physical data o primer 00020202 "t Ye to lu 176 ry y Ж Ж. nosno, sn,n, - я - "- lyu 177 si re | y - I'm snuo-snessn, SNSN, y with 178 all mem! 4 more - Zh Ko sno-snes-isn, SNSM,

R i s z» re 179 kn - Z I svosnens snen, im 45 Y and (ee) - pz "z" ime) bo b5 primer 7 s Ag E A / physical data

M

180 Ver r - mom | sleep, sleep

Zh r snyusnes-msn, 77 m 181 - mm | tolerable

J A snuSC-snes-zhsn, 1

C 2 182 - MO | snsn

Z snuF-snyaramsn, 77 oh My 183 sn(sN.), ry (amorphous) "H-NMR; -OSN,- sna snyamsn, 1.23; 1.26; 3.39-3.46; 4.0 . 185 E rya sNnusN, t. pl. 1037S

SS -osp,- LO snyu-mes s so « 186 s.n SsN,SN, t. pl.b22S povrai 1-7 -osn.- o sne you " 7 to " - t | snyun ne s | r snumsnEsSVsN , 77

Y m a 188 nya

I I snuyu-snestsn, Z t 3 | with 1» ES M (ee) - - 50

Thursday"

Ф) go bo b5 primer i o Ag E A // physical data -me and 189 si - t | snen, si M 0 not - - | sn.sn,

Fe ro sn,Ch-sNeS-M.SN, 7

M

191 Wh - s | snizn, y ry snuo-snes-M.sN, 7

M

192 Wh - t | snsn,

HA. X snUo-sNeb-M-CH, 7 ne m scho) will take 7 s Ag EA // physical data

Me Y - -0- snsn, t. pl. 187C 33rd moz snomes sha -

And with -

He 2 "- all ( y (2,0) "I 194 -0- snn, y snyutes p - amorphous "

Vg (8) s (E) -in . z" 195 -os- snen, that snyuchnes S

I - - t si (8) ( (ee) - tsu 5

Thursday"

F) name) because b5 example 7 Ge: Ag E A physical data 196 -0- sn,sn, / snu-mes zhd -,- nsvesn (8) (E) 197 n.e -osN,- snsn z-

IS

198 -oSN.- di obtusn, "HIRE: 3.98; 4.16; snu 4.49; 5.09; 6.82-7.56

Ich/mill.

Hg 199 sn, -osH,- di snyun, "H-NMR: 2.29; 3.95; snyumeos 4.15; 4.47; 4.71; 6.92- 7.82 h/mill. sn with c example 7 b Ag E A physical data

Me o) 290 si pl snsn, "H-NMR: 2.26; 3.99; -osy, - snumess 4.19; 4.5; 5.06; 6.67-7.62 h/mil. n .c "I 201 sn, tosnev, 'H-NMR: 2.17-2.29; sn -osn.- snUCH-mes 3.98; 4.14; 4.48; 4.96, -- with - 6.5-7.6 h/mill. "-- not (2.0) 202 sn snen 3. rai 27 h;E sn, -osn.- Vo sno neo " sn, 70203 sn, orosneyu, "N -NMR: 2.20; 228; no) with sn -OSN.- sno 3.97; 4.15; 4.46; 4.98; in with 6.68-7.58 h/mile. a g" (ee) shk shu 20

Thursday"

Ф) ko 6o 65 example 7 b Ag E A physical data still affects all ch2innnipua and current ope 205 sn,sn,

FI -osp,- To. Snyunes S

Y and 206 sn, snesn, -osn, shto bnen, ss rod - 207 s, -osn,- lo snesn, 208 sn -osn. sn,sn, "H-NMR: 1.195; 1.21; from sne 77 2.25; 2.82; 3.98; 4.15; 4.45; 5.0; 6.66- i-s, n, 7.58 h/mile. s ge o example 7. s Ag E A physical -Me dannie nn zh cho chi: zhi 9 chy7ninshvyshshetysh "U zo snu sn,sn, 2.34; 2.38, 3.98 ; 4.15; h: not 4.47; 4.97; 6.73- - 7.52 h/mile. d) 210 ra snomeso sn,sn, "Her -oSn,-

NsSES-NS-O 2 - o sn. ,

ChK" snisnsn, O (og) -y shu 20 "z"

Ф) ko bo 65 isychesky example 7 s Ag E A fF ie their data ooo (Y -- t ttlostshutt 214 amorphous? -osN.- sne snusn, H-NMR: 3.97; 4.13; 4.45; nusoMmenS 5.03; 6.86-8.50 h/ml. 215 ry "H-NMR: -osH.- sne sn,sn, 3.94; 3.97; 4.15; 4.47; nsomens 5, 02; 6.90 - 8.0 h/mile. 216. "H-NMR: -OSN"- som sn.,sn, 3.98; 4.15; then 4.47; 5.01; nisOoMeNS 6 ...

BO dn ' 'DYUU 218 osn, o su een, (8) sn,O-mes o

She o z - t. pl. 1332S

She

- Z "I zo ne M y 219 8) amor: no "-- psa snom snsn, u z shi H-NMR: ol, (soSiu) 6 -- 3.15 (5.3NU soosn, so y 220 amoi no mYatn and snyu-mes 0 svit, 5 ze

And from s - 3.80 « oh (53n) here? .

AND"

Sg" (o) shk shu "g" (F) ko 60 65 -D1-

example 7 with Ag E A -Me physical data 221 6) sn.sNn ra rai y

M M o-m-s t. pl. 220090

KK roles -

Ho) gu amorphous 222 -osn.- and sn,sn, ef snyu-neou "H-NMR: 3.97; 414; 4.46; 5.0; 6.91-7.54 h/mile. 223 CE , -osn.- r. sn,sn, amorphous snu "n-yaMR: 3.97; 4.14; 4.48; 5.03, 7.08-7.51 h/mill. 224 osn, o ry sn,sn, their She sn.o-me s' gamo y , z3O-M m rfno (s) se (is o example 7 b Ag E A physical data - zo M "se pp tp tane tent et nn nt non tya" pni ti flesh L. nn mine nm, chn acta tt nn antro chn. ch- p sn -osn, shto sn, "N-YAM:

From sleep Chneso 2.25; 40, "- 5.0; 5.86, 6.75-7.6 h/ml. with

SIXNu) with 226 -osn,- with where Dys -- 70 217 sn -osn.- r sleep nH-NMR: 8 s with sleep pu) 1.4; 23, 3.6- "» 4.5; 5.0; 6.8- " 7.6 chumilyal. t" (ee) The compound given in Table 1 as an example 60 can be obtained, for example, in the following way: si - with t" Mo o)

M o 2 "osn, co m so bo I

To the mixture 1.5 g (bmmol) 3-(5-methoxyimino-y-(2-hydroxy-phenyl)-methyl|-5,6-dihydro-1,4,2-dioxazine, 0.9 g (bmmol) 4, 6-dichloro-pyrimidine and 30 ml of M,M-dimethylformamide are added to an ice bath of 0.3 g (mmol) of sodium hydride suspension in bleached oil. After removing the ice bath, the reaction mixture is stirred at 20°C for 15 hours. therefore, it is concentrated in a vacuum created with the help of an oil pump, the residue is placed in a complex zylyl zifir of acetic acid, washed with water, dried over sodium sulfate and filtered.

They get 1.9g (8690 theory)

C-(0-Methoxyimino-o-(2-(b-chloro-pyrimidin-4-yl-oxy)-phenyl|-methyl)-5,6-dihydro-1,4,2-dioxazine as an oily residue.

The compound shown in Table 1 as example 61 can be obtained, for example, as follows:

SM

M c) g

AND

M. 2 o

M

- g "osn, 1779 0.

O,Zg mixture (0.9 mmol)

3-(0-methoxyimino-o-(2-(b-chloro-pyrimidin-4-yl-oxy)-phenyl|-methyl)-5,6-dihydro-1,4,2-dioxazine, 0.1 g s (O.U9mmol) 2-hydroxybenzonitrile, 0.1g (O0.9mmol) potassium carbonate, copper chloride (I) from the tip of the spatula and bml (o)

M,M-dimethylformamide is stirred for 15 hours at 1007°C. After that, it is concentrated in a vacuum created with the help of an oil pump, the residue is added to a complex Zytilovy acetic acid, washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated, and the residue is purified by chromatography on a column containing silica gel (solvent: hexane and acetone in a volume ratio of 7:3).

They receive O, Zg (8190 theories) h-

3-(d-Methoxyimino-α-(2-(6--2-cyano-phenoxy)-pyrimidin-4-yl-oxy)-phenyl|-methyl)-5,6-dihydro-1,4,2- dioxazin "- with a melting point of 8270.

The compound shown in Table 1 as an example 58 can be obtained, for example, in the following 99 way:

M co

I sh» 6) (ee) Mixture 0.5 g (2 mmol) 3-(0-methoxyimino-y-(2-hydroxy-phenyl)-methyl|)|-5,6-dihydro-1,4,2 -dioxazine, 0.3 g (2.2 mmol) of 2-methylbenzyl chloride, 0.4 g (2.5 mmol) of potassium carbonate and 100 ml of acetonitrile are heated under reflux for 15 hours. Then they are concentrated, the residue is placed in methylene chloride, washed with water, - dried over sodium sulfate and filtered. The solvent is carefully distilled from the filtrate under vacuum,

GT" received with the help of a water jet pump.

0.4 g (5990 theory) of 3-Hg-methoxyimino-α-(2-(2-methyl-benzyloxy)-phenyl/|-methyl)-5,6-dihydro-1,4,2-dioxazine with a melting point are obtained 14276.

The compound obtained according to example 1 can also be obtained, for example, in the following way: име) 60 b5

(9) and sn, sn,

M o g "osn,

AND; o 0.75 g (2.4 mmol) 3-(d-methoxyimino-o-(2-bromomethyl-phenyl)-methyl/|-5,b-dihydro-1,4,2-dioxazine and 0.70 g (b4 mmol) 2-methylphenol is dissolved in 15 ml of dimethylformamide, after cooling the mixture to -107C, 0.21g (7.0mmol) of 8095 sodium hydride is slowly added. After removing the cooling bath, the reaction mixture is stirred for 14 hours at a temperature of no more than 25"C, after then it is poured into water, taken in approximately twice its volume. After shaking in a mixture with 100 mM Zytil zephyr and acetic acid, the organic phase is separated, washed with 2N sodium hydroxide solution, dried over sodium sulfate and filtered. The solvent is carefully distilled from the filtrate at reduced pressure.

They get 0.40g (49960 theories)

3-(0-methoxyimino-o-(2-(2-methyl-phenoxy-methyl)-phenyl|-methyl)-5,6-dihydro-1,4,2-dioxazine (refractive index: pr? - 1, 5705).

The compound shown in Table 1 as Example 19 can be obtained, for example, as follows:

Sn, about: . « сн, сн, - «- 2 осн, с шчрФпитго « 0. 0.20g (0.5bmmol). M-(2-hydroxy-zthoxy)-o-methoxyimino-a-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetamide " is dissolved in 3 ml of chloroform and mixed at 02C with 0.25 g (1 .76 mmol) of phosphoric anhydride. The reaction mixture (ii) is stirred first for an hour at 20"C, and then for 4 hours at boiling, after which it is poured onto water, taken in approximately twice its volume, and shaken. After separate the organic phase and the aqueous phase three times additionally with chloroform. 84 mg (4296 theory) of 3-(d-methoxyimino-o-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-methyl)-5,6-dihydro-1,4,2 -dioxazine.

TN-NMR (O5 - DMSO, 5): 4.87; 3.84; 4.38; 4.10 parts per million - Obtaining the starting substances of the formula (IM): - 70 Example (IM - 1) s»

He

M. - o osn, o ny o oy 60 9.0 g (28 mmol) 3-(b0-methoxyimino-o-(2-tetrahydropyran-2-yl-oxy)-benzyl β-5,6b-dihydro-1, 4,2-dioxazine and 1.8 g of the ion exchanger HER 5ROS 108" in UOml of methanol are stirred for 15 hours at 2070. After that, the mixture is concentrated in a vacuum obtained with the help of a water jet pump, the residue is added to methylene chloride and filtered. The filtrate is concentrated in a vacuum obtained with the help of a water jet pump, and the residue is purified by chromatography on a column containing silica gel (solvent: hexane and acetone in a volume ratio of 7: 3). As the 1st fraction, O, bg is obtained (990 theory) 1-- 3-(o-methoxyimino-a-(2-hydroxy-phenyl)-methyl/d|-5,6-dihydro-1,4,2-dioxazine) in the form of an amorphous product, and in the quality of the 2nd fraction - C ,Zg (5090 theories)

E-(3-(d-methoxyimino-o-(2-hydroxy-phenyl)-methyl)-5,6-dihydro-1,4,2-dioxazine) with a melting point of 15370.

Obtaining the starting substances of the formula (IX):

Example (II - 1) (c) Fr

M and pine, "9 pit

To 6.g (9 mmol) of hydroxylamine hydrochloride in 290 ml of methanol add 13.9 g (211 mmol) of an 85905 aqueous solution of potassium hydroxide and 17 g (5 mmol) of complex methyl sulfur /o-methoxyimino-o-(2-tetrahydropyran-2-yl- oxy-phenyl)-acetic acid, after which the mixture of CM 29 is stirred for an hour at 407C. Then 7.7 g (5 mmol) of potassium carbonate were added, and 42.5 g (22 mmol) of 1,2-dibromoztane were added dropwise. The mixture is heated under reflux for 15 hours, and then condensed in a vacuum obtained with the help of a water jet pump. The residue is poured into methylene chloride, washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated, and the residue is purified by chromatography on a column containing silica gel (solvent: hexane and acetone in a volume ratio of 7:30:33). -

They get 9.Og (49960 theories)

3-(d-Methoxyimino-α-(2-tetrahydropyran-2-yl-oxy)-benzyl|-5,6-dihydro-1,4,2-dioxazine as 87 oily product. Ge)

Obtaining the starting substances of formula (X):

Zo Example (X - 1) M (8)

SA - with Ge; . and?

M

- Osn. shk o osn, because K solution 203g (1.81mol) tert. potassium butylate in 2 liters third. 564g (4.93mol) of butanol is added dropwise - tert. butyl nitrite and 411 g (1.64 mol) of complex methyl sulfur with 2-tetrahydropyranyloxy-phenylacetic acid, dissolved in 500 ml of tert. butanol. After 90 minutes, 350 g (2.47 mol) of methyl iodide are added dropwise, after which the mixture is stirred for 15 hours at 20"C. Then, in a vacuum, obtained with

Then, with the help of a water jet pump, the residue is poured into simple methyl-tert-butyl ether, dried over sodium sulfate and filtered. The residue is crystallized by digestion with diethyl ether, and the product is isolated by suction.

69.3 g (15,960 theory) of complex methyl ether o-methoxyimino-o-(2-tetrahydropyran-2-yl-oxy-phenyl)-acetic acid are obtained! with a melting point of 79"C.

Obtaining the starting substances of the formula (XII): ko Example (XII - 1) 60 b5

F o 07 pine,

A mixture of 500 g (3.0 mol) of complex methyl ester of 2-hydroxy-phenylacetic acid!, 506 bg (6 b, Omol)

3,4-dihydro-pyran, p-toluenesulfonic acid from the end of a spatula and 2.5 liters of tetrahydrofuran are mixed for 15 hours at 20"C, then mixed with 1095% of an ice-cold aqueous solution of potassium hydroxide, after which sodium sulfate is added The solvent is carefully distilled from the filtrate in a vacuum obtained with the help of a water jet pump.

698 g (9995 theory) of complex methyl sulfur 2-tetrahydropyranyloxy-phenylacetic acid are obtained as an oily residue.

Obtaining the original substances of the formula! (E):

Example (MI - 1)

Ve sn, s m. o osn,

Mmm so! "oh"-

0.5 g (2.1 mmol) 3-(3-methoxyimino-y-(2-methyl-phenyl)-methyl)|-5,6-dihydro-1,4,2-dioxazine and 0.57 g (32 mmol) M -bromo-succinimide is added to 1 Oml of tetrachloromethane and after adding 200 mg of azoisobutyronitrile, it is heated under reflux for 4 hours. After adding another 0.57 g (3.2 mmol) of M-bromo-succinimide, the mixture is heated under reflux for another hour. After that, it is cooled and filtered, the filtrate is concentrated, and the precipitate is subjected to chromatography on silica gel (solvent: toluene and acetone in a ratio of 10:1).

200 mg (3095 theory) of 3-(d-methoxyimino-o-(2-bromomethyl-phenyl)-methyl)-5,6-dihydro-1,4,2-dioxazine are obtained. "H-NMR (SOSI", 85): 4.4 parts per million.

M. - osn, i m sa bo o. -

To 19.6 g (0.283 mol) of hydroxylamine hydrochloride in 150 ml of methanol, slowly add a solution of 36.9 - (0.565 mol) of 86b95 potassium hydroxide in 150 ml of methanol. Then Zobg (0.145 mol) is added in portions

T" complex methyl zephyr o-methoxyimino-o-(2-methyl-phenyl)-acetic acid. The mixture is stirred for 3 hours at 50°C. Then, at 207°C, 20g (0.145mol) of potassium carbonate and 122g (0.65mol) of 1,2-dibromoethane are added. The reaction mixture is stirred for 17 hours at 65°C. After cooling, the mixture is filtered off, the filtrate is concentrated, and the precipitate is subjected to chromatography on silica gel (solvent: toluene and acetone in a ratio of 15:1). (F. 15.2g (4595 theory) of 3-(0-methoxyimino-o-(2-methyl-phenyl)-methyl|)|-5,6-dihydro-1,4,2-dioxazine are obtained. NMR (SOSI, 6): 2.2 parts per million.

Preparation of the starting substances of the formula (CHEM): 60 Example (CHEM - 1) b5 sn, 2 M 2 7 "osn, c) Osn, 70 187.5 g (1.67 Zmol) of potassium tert. butylate is dissolved in 1875 ml of tert. butanol. K to this solution, add a solution of 471.5 g (4.57 mol) of tert-butyl nitrite and 250 g (1.525 mol) of complex methyl sulfur with 2-methyl-phenyl-acetic acid in 500 ml of tert-butanol in such a way that the internal temperature does not exceed 50"С. The mixture is stirred for 90 minutes at 207 - 30"C. After that, 326.5 g (2.3 mol) of methyl iodide is added dropwise. The reaction mixture is stirred for 14 hours at 207C. Then /5 solvent is distilled off in a vacuum obtained with the help of a water jet pump , the residue is added to 2 liters of water and extracted three times with acetic acid.

After cooling to 0"C and stirring for 60 minutes, the crystallized product is bleached to 2° by suction.

84.5 g (2795 theory) of complex methyl sulfur o-methoxyimino-y-(2-methyl-phenyl)-acetic acid with a melting point of 53"С are obtained. 1TH-NMR (SOCI, 6): 2.19 parts per million .

Obtaining the original substances of the formula! (MIII): Ge 25 Example (MP! - 1) o sn, " 30 o - sn, sn, "-

M and "osn, p. 35 "(c); We

And osnenOon

0.5 g (2.3 mmol) of o-methoxyimino-a-|2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetic acid chloride is dissolved in 1 Oml of tetrahydrofuran. 0.26g (2.bmol) of tristhylamine is added to this solution. Then, 0.25 g (2.bmmol) of O-(2-hydroxy-ztyl)-hydroxylamine, dissolved in 1 Oml of tetrahydrofuran, is added dropwise at 8 s. The reaction mixture is stirred at 20°C for 2 hours. After that, it is poured into water and extracted with acetic acid. The extraction solution is dried over magnesium sulfate, concentrated and subjected to chromatography on silica gel (solvent: toluene and acetone in a ratio of 10:1). "g" Get 0.4 g (5090 theory) of M-(2-hydroxy-zthoxy)-o-methoxyimino-a-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetamide. 1TH-NMR (SOSI, 6): 3.65, 3.90, 9.15 parts per million - Obtaining the starting substances of the formula (XM): -oUu 70 Example (XM - 1) c» sn, - 59, (F) сн, сн, име) m. p осн, 60 o СИ 0.93g (2.95 mmol) o-methoxyimino-o-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|acetic acid is mixed with 4.0 g (2.9 mmol) of thionyl chloride and 5 mg of dimethylformamide, and the resulting mixture is stirred under reflux for 30 minutes. After that, the volatile component is carefully distilled off under reduced pressure.

0.95 g of o-methoxyimino-o-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetic acid chloride is obtained as an oily residue.

Example (XM - 2) Art. o sleep, sleep

M and g "osn, (9) on 2.0 g (b, immol) of complex methyl sulfur o-methoxyimino-o-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetic acid o dissolve in 20ml of 2% isopropanol. 30ml of 1N sodium hydroxide solution is added to this solution. Then the mixture is stirred for 14 hours at 40°C, after which it is poured into water. Then the pH value is adjusted to 6 with 2N sodium hydroxide solution, and the crystallized the product is isolated by ossification.

1.5 g (7895 theory) of o-methoxyimino-o-(2-(2,4-dimethyl-phenoxy-methyl)-phenyl|-acetic acid are obtained. 1TH-NMR (SOCI", 6): 3.9; 4 .85 parts per million

An example of testing new active substances

Example A

Opiate with Rugeporgoga and (hegesis (barley)) in/protective action

Solvent: 10 parts by weight of M-methylpyrrolidone

Emulsifier: 0.6 parts by weight of simple alkylarylpolyglycol resin "I

To obtain the expediently used preparation of the active substance ives. part of the active substance is mixed with specified amounts of solvent and emulsifier, and the resulting concentrate is diluted with water to the desired concentration. -

To study the protective action, young plants are sprayed with the active substance preparation until droplets are formed. After application of the drug, the plants are sprayed with a conidial suspension

Then the plants are kept in an incubation chamber for 48 hours at a temperature of 20°C and a relative humidity of 100905.

After that, the plants are stored in a greenhouse at a temperature of about 207C and a relative humidity of about 80905.

7 days after inoculation, an assessment is carried out.

At the same time, they establish that the degree of activity, for example, of the compound of example 1 is 10095 at a consumption of 400 g per hectare. and Example B "» Opiate with Rpuyuriinoga (tomato)/systemic action

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.6 parts by weight of a simple alkylaryl polyglycol zephyr. part of the active substance is mixed with specified amounts of solvent and emulsifier, and the resulting concentrate is diluted with water to the desired concentration. -th For the study of systemic properties, the preparation of the active substance is poured onto the soil in which there are 20 young plants ready to be replanted. A day after treatment, plants are inoculated with a water suspension of spores of RPpuiorpygoga Ipieviapzv.

Then the plants are stored in an incubation chamber at a temperature of about 207C and a relative humidity of 10096.

On the day after inoculation, an assessment is carried out.

At the same time, they establish that the degree of activity, for example, of the compound of example 1, is 5895 at a concentration of the active substance of 100 ppm. o Example In the name) Opiyt with Rugisshagia (rys) uusystemnoe edie

Solvent: 12.5 parts by weight of acetone 60 Emulsifier: 0.3 parts by weight of simple alkyl aryl polyglycol sulfur

To obtain the expediently used preparation of the active substance ives. part of the active substance is mixed with the indicated amount of solvent, and the resulting concentrate is diluted with water and the indicated amount of emulsifier to the desired concentration.

To study the systemic properties, 40 ml of the active substance preparation is poured onto the soil in which 65 V young rice plants have grown. 7 days after treatment, the plants are inoculated with an aqueous suspension of spores of Rugisciagia ogulae. After that, the plants are stored in a greenhouse at a temperature of 25°C and a relative humidity of 100-905 until the assessment is carried out.

4 days after inoculation, the lesion is assessed.

At the same time, they establish that the degree of activity, for example, of the compound of example 1, is 8095 at a consumption of 100mg/10Oml.

Claims (1)

Formula of the invention 70 1. Substitution of azadioxacycloalkene of the general formula (I) is represented by the following formula: where A is unsubstituted or substituted alkanediyl (alkylene), Ag is unsubstituted or substituted arylene or heteroarylene, and E is 1-alkene-1,1-diyl having a radical in position 2, 2-aza-1-alkene-1,1-diyl having a radical in position 2, 3-oxa- or 3-thia-1-propene-2,3-diyl having a radical in position 1 radical in 3-aza-1-propene-2,3-diyl, having a KK radical in the C position and a B radical in the 1 position, 1-aza-1-propene-2,3-diyl having a 22 radical in the 1 position, З- oxa- or 3-thia-1-aza-propene-2,3-diyl, having an e2 radical in the 1 position, 1,3-diaza-1-propene-2,3-diyl, having a К and в radical in the 3 position position 1 radical B2 or an unsubstituted or substituted imino group (, azamethylene", M-K 3, and K means alkyl, B! - hydrogen, halogen, cyano or unsubstituted or substituted alkyl, alkoxy, alkylthio-, ch » an alkylamino- or dialkylamino group, B2-hydrogen, amino, cyano or unsubstituted or substituted alkyl, o alkoxy, alkylamino- or dialkylamino group, B-hydrogen, cyano or unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, b - simple bond, oxygen, unsubstituted or substituted by halogen, hydroxyl, alkyl, "g With Hhaloalkyl or cycloalkyl, alkanediyl, alkenediyl, oxalkenedyyl, alkynediyl or one of the following groups: - -9-69-, -69-9-, -СН-О-, -0-СН-, -С00-9-СНое-, -СН-О-С2О-, -9-59-СН»-, - 0-509-9-СН-, -М-М-, -5(0)р-, "- -СНо-8(О)п-, -СО-, -8(О)4-СНо-, - С(Б7)-М-О-, -С(27)-М-ОО-СН»-, -МЩ(Б2)-, -СО-Мщ(5)-, -Щ(5)-са-, - 9-СО-М(Е)-, -М-с(Б7)-0-СНо-, -СНо-О-М-С(87)-, -М(85)-сСО-0-, са-м (5)-са-а-, -М(5)-СО-0-СНо-, -СО-СНо- or со -М-М-с(В7 )-М-О-, and n means the number 0, 1 or 2, O is oxygen or sulfur, " B" - hydrogen, cyano or unsubstituted or substituted alkyl, alkoxy, alkylthio-, alkylamino-, dialkylamino group or cycloalkyl, hydrogen, hydroxyl, cyano or unsubstituted or substituted alkyl, alkoxy or cycloalkyl, and " 7 - unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl. - t0 2. Compounds of formula (I) according to point 1, where c A means alkanedyl with 1 - carbon atoms, unsubstituted or substituted by halogen, alkyl or haloalkyl with 1 - 4 carbon atoms, Ag - unsubstituted or substituted phenylene or naphthylene, or heteroarylene with 5 or more ring members, of which at least one represents oxygen, sulfur or nitrogen, and, if necessary, one or two more represent nitrogen, and the possible substituents used are selected from the groups , is including: (ee) halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, unbranched with or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon atoms, unbranched or branched alkenyl, alkenyloxy or alkynyloxy, each with 2 - 6 - 20 0 carbon atoms, unbranched or branched haloalkyl, haloalkyl, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, each with 1-6 carbon atoms and 1-13 identical T" or different halogen atoms, unbranched or branched haloalkyenyl or haloalkenyloxy, each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, unbranched or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl, each with 1-b atoms HF) of carbon in separate alkyl parts, unsubstituted or at least monosubstituted by the same or different substituents from among halogen and/or unbranched or branched alkyl with 1-4 carbon atoms and/or unbranched or branched haloalkyl with 1-4 carbon atoms and 1 - 9 identical or different halogen atoms, double-bonded alkylene or dioxyalkylene with 1 - 6 60 carbon atoms, E is one of the following groups: b5 fev Ze jaLhst yar ZKU pe no 1 and 2 no 1 her 2 in" E E "r E, ' ' ' ' Y - oxygen, sulfur, methylene or alkylimino group, K - alkyl with 1 - b carbon atoms, 0 B - hydrogen, halogen, cyano or unsubstituted or substituted by halogen, a cyano group or an alkyl with 1 to 4 carbon atoms, an alkyl, alkoxy, an alkylthio group, an alkylamino or a dialkylamino, each with 1 to 6 carbon atoms in the alkyl residues, B2 - hydrogen, amino, cyano, or unsubstituted or substituted by a halogen, cyano group, or alkyl with 1 to 4 carbon atoms, alkyl, alkoxy, alkylamino, or dialkylamino, each with 1 to 2 carbon atoms in /5 In each of the remainders, BZ - hydrogen, cyano, or unsubstituted or substituted by halogen, cyano group, or alkyl with 1-4 carbon atoms, alkyl, alkenyl, and alkynyl, each with 1-b carbon atoms, or unsubstituted or substituted by halogen, cyano group, carboxyl, alkyl with 1-4 atoms of carbon or alkoxycarbonyl with 1 - 4 carbon atoms, cycloalkyl and cycloalkylalkyl with 3 - b carbon atoms in the cycloalkyl parts and 1 - 4 carbon atoms in the alkyl part, Сб - a simple bond, oxygen, unsubstituted or substituted by halogen, hydroxyl, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms or cycloalkyl with 3-b carbon atoms, alkanediyl, alkenedyl, oxalkenedyl, alkyndiyl or one of the following groups -90-с9-, -90-9-, -СН-О-, -9-СН-, -СО-9-СН»-, -«СН-О-СО-, с -9-69-СНо-, 9-С9-0-СНо-, -MA M-, -5(0)4-, -СНо-5(О)4-, -СО-, -(О)п-СН»-, -С(В7 )-М-О-, -С(87)-М-ОО-СН», -Ш(2)-, -СО-М(В5)- , i9) -М(85)-сО-, -0-сО-Щ(25)-, -М-С(87)-0-СН»-, -СНо-О-М-С(В7)-, -Ш(25)-сСО-9-, -СО-Ш(25)-са-0-, -ШШЕЗ)-СО-0-СН»-, -«СО-СН»- or -М-М-С (B7)-M-O-, and n means the number 0, 1 or 2, "I O - oxygen or sulfur, "- B - hydrogen, cyano, unsubstituted or substituted by halogen, cyano or alkyl with 1-4 carbon atoms alkyl, alkoxy-, alkylthio-, alkylamino-, dialkylamino group, each with 1-b carbon atoms in -- alkyl groups, or unsubstituted or substituted halogen, cyano, carboxyl, alkyl with 1-4 (Ф carbon atoms or alkoxycarbonyl with 1-4 carbon atoms, cycloalkyl with 3-b carbon atoms, B - hydrogen, hydroxy, cyano or unsubstituted or substituted by halogen, cyano or 1-4 alkyl with carbon atoms, alkyl with 1-b carbon atoms, or unsubstituted or substituted by halogen, cyano, carboxy, alkyl with 1-4 carbon atoms, or alkoxycarbonyl with 1 - 4 carbon atoms cycloalkyl with 3 - 6 carbon atoms, " 7 - alkyl with 1 - 8 carbon atoms, unsubstituted or substituted by halogen, cyano, hydroxyl, amino, C 70 alkyl with 1-4 carbon atoms, alkylthio group with 1-4 carbon atoms, alkylsulfinyl with 1-4 carbon atoms or alkylsulfonyl with 1-4 carbon atoms, unsubstituted or substituted by halogen, unsubstituted or substituted by halogen alkenyl and alkynyl, each with 1 - 8 carbon atoms, cycloalkyl with 3 - b carbon atoms, unsubstituted or substituted by halogen, cyano, carboxyl, phenyl, unsubstituted or substituted halogen, cyano, alkyl with 1 - 4 carbon atoms, 75 haloalkyl with 1 - 4 carbon atoms, C 1 - 4 alkyl or C 1 - 4 haloalkyl, C 1 - 4 alkyl or C 1 - 4 oxycarbonyl, unsubstituted or substituted phenyl, naphthyl or (if necessary, benzanellated) heterocyclyl with 5 or 6 ring members, of which at least one represents oxygen, sulfur or nitrogen and, if necessary, one or two further members represent nitrogen, with a possible substituent and choose -k 70 preferably from the group including oxygen (instead of two geminal hydrogen atoms), halogen, cyano-, nitro-, amino group, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, unbranched or T» branched alkyl, alkoxy, alkylthio group, alkylsulfinyl or alkylsulfonyl, each with 1-b carbon atoms, unbranched or branched alkenyl or alkenyloxy, each with 2-b carbon atoms, unbranched or branched haloalkyl, haloalkyl, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, each with 1-6 carbon atoms and 1 13 identical HF) or different halogen atoms, unbranched or branched haloalkenyl or haloalkenyloxy, each with 2 to 2 carbon atoms or 1 to 13 identical or different halogen atoms, unbranched or branched alkylamino group, dialkylamino group, alkylcarbonyl, alkyloxycarbonyloxy, alkyloxycarbonyloxy, hydroxyalkyl or alkoxy minoalkyl, each 60 with 1-6 carbon atoms in separate alkyl parts, unsubstituted or at least mono-substituted with the same or different halogen residues and/or unbranched or branched alkyl with 1-4 carbon atoms and/or unbranched or branched haloalkyl with 1-4 atoms carbon and 1 - 9 identical or different halogen atoms, double bond alkylene and dioxyalkylene, each with 1 - b carbon atoms, cycloalkyl with 3 - b carbon atoms, heterocyclyl or heterocyclylmethyl, each with 3 - 7 ring members, of which 1 - Z are identical or -BO0- by various heteroatoms, in particular, nitrogen, oxygen and/or series atoms, as well as unsubstituted or at least monosubstituted in the phenyl part by the same or different residues from groups including halogen, cyano, nitro, carboxy, carbamoyl, and/or unbranched or branched alkyl 51 - 4 carbon atoms and 1 - 9 identical or different halogen atoms and/or unbranched or branched haloalkyl with 1 - 4 carbon atoms and/or unbranched or branched haloalkyl with 1 - 4 carbon atoms and 1 - 9 identical or different halogen atoms and / or alkylcarbonyl or alkoxycarbonyl with 1 to 5 carbon atoms, phenyl, phenoxy, benzyl, phenylaztyl or phenylosthyloxy. 70 Z. Combinations of formulas! (I) according to point 1, where A - methylene or dimethyl (stan-1,2-diyl), unsubstituted or substituted by residues from the groups including fluorine, chlorine, methyl, zyl or trifluoromethyl, Ag - unsubstituted or substituted ortho-, meta- or para-phenylene, as well as furandiyl, thiophendiyl, pyrroldiyl, pyrazoldiyl, triazoldiyl, oxazoldiyl, isoxazoldiyl, thiazoldiyl, isothiazoldiyl, /5 oxadiazoldiyl, thiadiazoldiyl, pyridinediyl, pyrimidindiyl, pyridazindiyl, pyrazindiyl, 1,3,4-triazindiyl or 1,2,3-triazindiyl, and the possible substituents are chosen, in particular, from groups including fluorine, chlorine, cyano, methyl, ztyl, trifluoromethyl, methoxy, ztoxy, methylthio, methylsulfinyl or methylsulfonyl, E - one of the following groups: 20 t ze yacht yad Z KE Mo ni ; Mode ве, сч 25 where o U is oxygen, sulfur, methylene, or alkylimino, K is methyl, ztyl, n- or isopropyl, n-, iso-, or second. butyl, B - hydrogen, fluorine, chlorine, bromine, cyano or methyl, xtyl, propyl, methoxy, ztoxy, methylthio-, xtylthio-, methylamino-, xtylamino- or dimethylamino group, unsubstituted or substituted by residues from the groups, Z 30 including fluorine, chlorine, cyano, methoxy and ztoxy, "- V? - hydrogen, amino, cyano or methyl, ztyl, methoxy, ztoxy, methylamino-, ztylamino- or dimethylamino group, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, 1"7 methoxy or ztoxy, and co BZ - hydrogen, cyano or methyl, ztyl, n- or isopropyl, n-, iso- or sec-butyl, unsubstituted or 35 substitution with residues from the group including fluorine, cyano, methoxy and ethoxy, allyl, propargyl or C cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, unsubstituted or substituted with residues from the group including fluorine, chlorine, cyano, carboxy, methyl, zyl, n- or isopropyl, methoxycarbonyl or z-oxycarbonyl, " b is a simple bond, oxygen, methylene, dimethyl (ztane-1,2-diyl), ztene-1,2-diyl, ztyn-1,2-diyl, - t0 unsubstituted or substituted by residues from the group including fluorine, chlorine , hydroxy, methyl, ztyl, n- or c isopropyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or one of the following From" groups -9-69-, -69-9-, -СН-О-, -0-СН-, -С00-9-СНое-, -СН-О-С2О-, -9-59-СН»-, - 0-509-9-СН-, -М-М-, -5(0)р-, -СНо-8(О)п-, -СО-, -8(О)0-СНо-, -С(Б)М-О-, -С(Б7)-М-О-СНо-, -МЩ( B5)-, -СО-Мщ(Б5)-, -Щ(5)-сО-, -4-сCO-шЩ(2)-, iz -mes(27)-0-CH"-, "СНо-О-М-с(Б7)-, -(А85)-сО-0-, -"СО-М(5)-С0-0- or -M(25)-CO-0-CH"-, while so n means the number 0, 1 or 2, - O - oxygen or sulfur, B - hydrogen, cyano, methyl, ztyl, n- or isopropyl, n-, iso- or ret. butyl, methoxy, zthoxy, propoxy, - butoxy, methylthio-, zylthio-, propylthio-, butylthio-, methylamino-, zylamino-, propylamino-, dimethylamino- or a distylamino group, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, methoxy or zoxy, or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, carboxyl, methyl, zyl, n- or isopropyl, Methoxycarbonyl or zthoxycarbonyl, i B - hydrogen, hydroxyl, cyano or methyl, ztyl, n- or isopropyl, n-, iso- or s. butyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, methoxy or ztoxy, or cyclopropyl, as cyclobutyl, cyclopentyl and cyclohexyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, cyano, carboxy, methyl, zyl, n- or isopropyl, methoxycarbonyl or zoxycarbonyl, and in 27 - methyl, zyl, n- or isopropyl, n -, iso-, sec.-- or tert. butyl, unsubstituted or substituted with residues from the group consisting of fluorine, chlorine, bromine, cyano, hydroxy, amino, methoxy, ztoxy, methylthio, zylthio, methylsulfinyl, zylsulfinyl, methylsulfonyl, zylsulfonyl, unsubstituted or substituted with fluorine and/or bromine, allyl, crotonyl , 1-methylallyl, propargyl and 1-methylpropargyl, unsubstituted or substituted by residues from the group including fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl 65 ml of cyclohexyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, bromine, cyano, carboxy, phenyl, unsubstituted or substituted by residues from the group including fluorine, chlorine, bromine, cyano, methyl, ztyl, n- or isopropyl, n-, iso-, sec.- or tert. butyl, trifluoromethyl, methoxy, ztoxy, n- or isopropoxy, difluoromethoxy and trifluoromethoxy, methyl, ztyl, n- or isopropyl, methoxycarbonyl or ztoxycarbonyl, n-, iso-, secondary- or tert. butyl, trifluoromethyl, methoxy, ztoxy, n- or isopropoxy, difluoromethoxy or trifluoromethoxy, unsubstituted or substituted phenyl, naphthyl, furyl, tetrahydrofuryl, benzofuryl, tetrahydropyranyl, thienyl, benzothienyl, pyrrolyl, dihydropyrrolyl, tetrahydropyrrolyl, benzopyrrolyl, benzodihydropyrrolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, isothiazolyl, imidazolyl, benzimidazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4--riazinyl or 1,3,5-triazinyl, wherein 7/0 Possible substituents are preferably selected from groups including oxygen (instead of two geminal hydrogen atoms), fluorine, chlorine, bromine, cyano-, nitro-, amino group, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; methyl, ztyl, n- or isopropyl, n-, iso-, sec.- or tert. butyl, methoxy, ztoxy, n- or isopropoxy, methylthio, ztylthio, n- or isopropylthio, methylsulfinyl, ztylsulfinyl, methylsulfonyl or ztylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, 7/5 trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ztylamino, n - or isopropylamino, dimethylamino, distylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, zthoxycarbonyl, methylsulfonyloxy, zthylsulfonyloxy, hydroxyiminomethyl, hydroxyminostyl, methoxyiminomethyl, zthoxyminomethyl, methoxyminostyl or zthoxyminostyl; trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, unsubstituted or at least monosubstituted with the same or different residues from the group consisting of fluorine, chlorine, methyl, xyl, n- or isopropyl, and also phenyl, phenoxy, benzyl or benzyloxy, unsubstituted or at least monosubstituted in the phenyl part with the same or different residues from the group including fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl, methyl, zyl, n- or isopropyl, n-, iso-, second- or third. butyl, trifluoromethyl, methoxy, zthoxy, n- or isopropoxy, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl with ov M zthoxycarbonyl. 4. Compounds of the formula (I) according to point 1, where i) A is dimethyl (stan-1,2-diyl), Ag is ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl, E - one of the following groups: "E 309 st "- no 1 shd 2 - e. is, so pe 2 " K ik mean methoxy, C - oxygen, methylene or one of the following groups -сно-О-, -О-СН»-, -"Б(О)п-, -"СНо-8 (О)а-, -8(О)y-СНо, -С(Б7)-М-О-, -0-м-с(Б7)-, -С(Е7)-М-О-СН»- , -M(B2)- or -"СНо-О-М-С(Б7), " where т с н is the number 1, 2 or З, and B is hydrogen, methyl, or methyl, and B is hydrogen, methyl or zyl, and 7 - unsubstituted or substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, with possible substituents! from groups including fluorine, chlorine, bromine, cyano, methyl, methyl, n- or isopropyl, n-, iso-, secondary- or tert. butyl, methoxy, o zthoxy, n- or isopropoxy, methylthio, zylthio, n- or isopropylthio, methylsulfinyl, zthylsulfinyl, methylsulfonyl or zthylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, - trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ztoxiccarbonyl, -- uU 270 methoxyiminomethyl, ztoxyminomethyl, methoxyminostyl, ztoxyminostyl, methylenedioxy and ethylenedioxy, unsubstituted or at least monosubstituted with the same or different residues from the groups including fluorine, chlorine, methyl or methyl, phenyl, phenoxy, benzyl and benzyloxy, unsubstituted or in phenyl parts are at least monosubstituted by the same or different residues from groups including fluorine, chlorine, bromine, cyano, methyl, zyl, n- or isopropyl, n-, iso-, secondary- or tert. butyl, trifluoromethyl, methoxy, ztoxy, n- or isopropoxy, difluoromethoxy and trifluoromethoxy. o 5. Fungicides that differ in that they contain at least one compound of the formula (I) according to item 1. where 6. A method of combating unwanted fungi that differs in that the compounds of the formulas! (I) according to point 1, mushrooms and/or their biotope are processed. 60 7. The method of obtaining azadioxacycloalkenes of the general formula (I) according to item 1, characterized by the fact that a) the production of carboxylic acid of the general formula (II) (9) t vv ov Innu; 65 where Ag, E, b and 7 have the above-mentioned meaning, a K means alkyl, in the first stage they are subjected to interaction with hydroxylamine or its hydrogen halide salt, if necessary, in the presence of an acid acceptor and, if necessary, in the presence of a diluent, and in the second stage in situ, i.e. without intermediate separation of the reaction product of the first stage, are subjected to interaction with disubstituted alkanes of the general formula (III) Х-А-Х, (PP) where A has the above-mentioned value, and 70 X means halogen, alkylsulfonyloxy or arylsulfonyloxy, if necessary, in the presence of an acid acceptor! and, if necessary, in the presence of a diluent, or, b) in the case that in formula (I) b means oxygen or the group -CHN-O-, and A, Ag, E and 7 have the above-mentioned meaning, hydroxyaryl compounds of the general formulas (IM) yo ra Y ;/2 no Oso go where A, Agy E have the above-mentioned meaning, subject to interaction with compounds of general formulas! (M) 24SNadh, (M where X and 7 have the above meaning, and t means the number 0 or 1, if necessary, in the presence of an acid acceptor! and, if necessary, in the presence of a diluent, with subsequent, if necessary, translation group 7 to the desired value by conventional methods, or, that c) in the case that in formula (I) C means the group -2-CH»-, and A, Ag, E and 7 have the above-mentioned value, - halomethyl compounds of the general formulas ! (MI) "- Ш79 І ецяти і-і на і х- SN. (9) SLU with where "And A, Ag and E have the above-mentioned meaning, and X! means halogen, are subjected to interaction with compounds of general formulas! (MII) « 2-9-H, (MI) where ts o and 7 have the above-mentioned meaning, and if necessary, in the presence of an acid acceptor! and, if necessary, in the presence of a diluent, "» or, that d) hydroxyalkoxyamides of the general formula (MIP) Nori» A and Ag Z on tya so za Eto , SUP) - where A, Ag, E, C and 7 have the above meaning, - they are subjected to cyclization with a water-removing agent, if necessary, in the presence of a diluent. Article 8. Compounds of formulas (I) according to point 1 as fungicides. 9. The method of obtaining fungicidal agents, characterized by the fact that the compounds of formula (I) according to point 1 are mixed with fillers and/or surface-active substances. Official bulletin "Industrial Property". Book 1 "Inventions, useful models, topographies of integral F, microcircuits", 2002, M 8, 15.08.2002. State Department of Intellectual Property of the Ministry of Education and Science of Ukraine. 60 b5