2-[1', 2', 4'-triazole-3'-roximation]anilide, intermediate products and the means of combating harmful fungi

 

(57) Abstract:

Describes the new connection- 2-[1', 2', 4' - triazole-3'-roximation] anilide General formula (I), where R1means C1- C4alkyl, halogen, R2means hydrogen, halogen, C1- C4alkyl, C1- C4halogenated, C1- C4alkoxygroup, R3means C1- C4alkyl, phenyl, unsubstituted or substituted by 1 to 2 halogen atoms, WITH1- C6the alkyl, C1- C4haloalkyl, nitro, C1- C4alkoxyl, C1- C4haloalkoxy, phenyl or fenoxaprop, 2-pyridyl, unsubstituted or substituted C1- C4haloalkyl, 2-pyrazinyl or pyridyl substituted by halogen, 4means hydrogen or C1- C4alkyl, R5means C1- C4alkyl, X represents oxygen or NH, n = 0 or 1. The compounds exhibit biological activity and can be used to control pests and harmful fungi with higher efficiency. Describes the intermediate products and the means of combating harmful fungi. 3 C. p. F.-ly, 3 PL.

The invention relates to 2-[1',2',4'-triazole-3'-roximation] anilides formula I

< / BR>
W is t be various, if n is greater than 1;

X represents a direct bond, O, or NRa;

Rameans hydrogen, alkyl, alkenyl, quinil, cycloalkyl or cycloalkenyl;

R1means nitro, cyano, halogen, optionally substituted alkyl, alkenyl, quinil, alkoxy, alkenylacyl, alkyloxy or

if n is 2, additionally represents associated with two adjacent ring atoms optionally substituted by a bridge containing three or four members from the group containing 3 or 4 carbon atoms, 1-3 carbon atoms and 1 or 2 nitrogen atom, oxygen and/or sulphur, and this bridge together with the ring to which it is linked, may form a partially unsaturated or aromatic radical;

R2means hydrogen, nitro, cyano, halogen, C1-C4alkyl, C1-C4halogenated, C1-C4alkoxy, C1-C4alkylthio or C1-C4alkoxycarbonyl; R3means optionally substituted alkyl, alkenyl or quinil; optionally substituted saturated or mono - or doubly unsaturated cycle which together with the carbon atoms may contain one to three heteroatoms as members of a cycle of the following: oxygen, sulfur and nitrogen, or the optional kachestve members cycle from one to four nitrogen atoms or one or two nitrogen atom and one oxygen atom or sulfur, either one oxygen atom or sulfur;

R4means hydrogen, optionally substituted alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, alkylaryl or alkoxycarbonyl;

R5means alkyl, alkenyl, quinil, cycloalkyl or cycloalkenyl or if X is NRaadditionally represents hydrogen.

In addition, the invention relates to a method and intermediate products for obtaining these compounds, to the containing means, and also to their use for combating agricultural pests and harmful fungi.

From the international application WO-A 93/15046 known 2-[1,2,4-triazole-5-roximation] anilide used to control pests and harmful fungi.

The basis of the invention was based on the task to get a connection with a higher efficiency.

In line with this, there were obtained the compounds of formula I, defined above. In addition, they found the method and intermediate products for their production, the developed formulation containing their mixtures, as well as a way of combating agricultural pests and parasitic fungi using the compounds of formula I.

Link is tons of hydrogen, and X represents a direct bond or oxygen, and receive, for example, due to the fact that the derivative of benzyl of the formula II in the presence of a base interaction with the 3-hydroxytriazolam formula III is transferred to the corresponding 2- [1,2,4-triazole-3-roximation] nitrobenzene of the formula IV, the compound IV to restore N-hydroxylysine formula Va and this connection Va with carbonyl compounds of the formula VI are transforming the compound of formula I (scheme 1, is provided at the end of the description).

The etherification of the compounds of formulas II and III is carried out usually at temperatures in the range of 0oC to 80oC, preferably in the range of 20oC to 60oC.

Usable solvents are aromatic hydrocarbons, such as toluene, ortho-, meta - and para-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, NITRILES, such as acetonitrile and propionitrile, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, ketones, such as acetone and methyl ethyl ketone, and dime is in; preferred of them methylene chloride, acetone, toluene, tert-butyl methyl ether and dimethylformamide. Be used can also mixtures of these solvents.

As grounds may be considered, in principle, inorganic compounds, such as hydroxides of alkali and alkaline earth metals (e.g. lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkaline oxides and alkaline earth metal (such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide), hydrides of alkali and alkaline earth metals (e.g. lithium hydride, sodium hydride, potassium hydride and calcium hydride), amides of alkali metals (e.g. lithium amide, sodium amide and potassium amide), carbonates of alkali and alkaline earth metals (for example, lithium carbonate and calcium carbonate, and hydrogen carbonate of alkali metals (e.g. sodium bicarbonate), ORGANOMETALLIC compounds, especially alkali alkali metals (for example, motility, utility and finality), alkylhalogenide magnesium (for example, methyl chloride magnesium), and alcoholate of alkali and alkaline earth metals (for example, methanolic sodium, ethanolic sodium, ethanolic potassium tert-butanolate potassium and dimethoxymethane), creatinin and N - methylpiperidin, pyridine, substituted pyridine, such as kallidin, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particularly preferred among them are sodium hydroxide, potassium carbonate and tert-butanolate potassium.

The base is used generally in equimolar amounts with excess or use them if necessary as solvents.

For a successful reaction, it may be appropriate to add catalytic amounts of crown ethers (for example, 18-crown-6 or 15-crown-5).

The above reaction can be carried out in a two-phase mechanism, comprising a solution of hydroxides or carbonates of alkali or alkaline earth metals in water and the organic phase (for example, aromatic and/or halogenated hydrocarbons). As phase transfer catalysts can be used, for example, halides and tetrafluoroborate ammonium (e.g., chloride of benzyltriethylammonium, bromide of benzyltrimethylammonium, tetrabutylammonium chloride, bromide of hexadecyltrimethylammonium or tetrafluoroborate tetrabutylammonium), as well as the halides of phosphonium (e.g., chloride tetrabutylphosphonium and bromide tetraphenylporphine).

For successful Oswestry in the appropriate hydroxylate, which is then subjected to interaction with a derivative of benzyl.

The initial compounds of the formula II required for obtaining compounds of formula I, are known from European application EP-A 513580 or can be received as described in this publication methods [see Synthesis 1991. 181; Anal. Chim. Acta 185. 295 (1986);EP-A 336567].

3-Hydroxytriazolam formula III are also known from the patent literature or can be obtained as described in publications methods [Chem. Ber. 56. 1794 (1923); DE-A 2150169; DE-A 2200436; US-A 4433148; J. Med. Chem. 33, 2772 (1990); Synthesis 1987, 986; DE-A 2260015; DE-A 2417970].

The restoration of the nitro compounds of formula IV to the corresponding N-hydroxyamino formula Va perform similarly known from the literature methods, for example, using metals such as zinc [Ann. Chem. 316. 278 (1901)], or hydrogen (EP-A 085890).

The exchange reaction between N-hydroxyanisole Va and carbonyl compounds VI is carried out in alkaline conditions, particularly preferably at temperatures in the range -10oC to 30oC. To a preferred solvents include methylene chloride, toluene, tert-butyl methyl ether or ethyl ester of acetic acid. To preferred bases include sodium bicarbonate, potassium carbonate, sodium hydroxide or vodem value other than hydrogen, and X represents a direct bond or oxygen, can be obtained, for example, due to the fact that the derivative of benzyl of the formula IIa is first reduced to the corresponding hydroxyanisole formula Vb, then this hydroxyanisol Vb interaction with the carbonyl compound of formula VI is transferred to the appropriate anilide formula VII, then anilide VII interaction with the compound of the formula VIII transform into the amide of formula IX, then this amide IX translated into the appropriate benzylamine formula X, which in the presence of a base interaction with the 3-hydroxytriazolam formula III are transforming the compound of formula I (scheme 2, at the end of this description).

The reaction is carried out analogously to the above methods.

Halogenoalkane compounds of formula IX are carried out by a radical mechanism, using for these purposes, such halogenation agents, such as N-chloro - or N-bromosuccinimide, elemental halogen (e.g. chlorine or bromine) or thionyl chloride, sulfurylchloride, trichloride phosphorus or pentachloride phosphorus and other similar compounds. Usually used additional initiator radical reactions (e.g., azobisisobutyronitrile) or reactice in the usual organic diluent.

Another possibility of obtaining compounds of the formula I, in which R4does not mean hydrogen, is that the corresponding compound of formula I, in which R4is hydrogen, is subjected to the interaction with the compound of the formula VIII (scheme 3, is provided at the end of the description).

This reaction is carried out by known methods in an inert organic solvent in the presence of a base at temperatures in the range -20oC to 50oC.

As the grounds are primarily sodium bicarbonate, potassium carbonate, sodium hydroxide and aqueous solutions of sodium hydroxide.

As solvents used primarily acetone, dimethylformamide, toluene, tert-butyl methyl ether, ethyl ether, acetic acid and methanol.

The preferred way of preparing compounds of the formula I, in which X represents NRais that benzylaniline formula IXa transferred to the appropriate benzylamine formula Xa, then the halide Xa in the presence of a base interaction with the 3-hydroxytriazolam formula III is transferred to the compound of the formula I. a and b end connection I. And interaction with the amine of formula XI transform in Southend Ha and conversion benzylchloride Xa connection I. A exercise, typically, and preferably in the above-described conditions.

The interaction of compounds of formula I. A primary or secondary amines of the formula XIA, XIb, respectively is carried out at temperatures in the range of 0oC to 100oC without solvent or in an inert solvent or solvent mixture.

As solvents suitable primarily water, tert-butyl methyl ether and toluene or a mixture thereof. To improve the solubility of doctow it may be appropriate to additionally add one of the following solvents (as agents of dissolution): tetrahydrofuran, methanol, dimethylformamide and etilenglikolevye ether.

Amines XIa, XIb, respectively applied usually in excess of 100% with respect to compounds or they can be used as solvents. To improve yield, it may be appropriate to carry out the reaction under pressure. Obtaining compounds of the formula I is carried out through the stage of formation of intermediate products of the formula XII

< / BR>
in which the substituents and the index have the following meanings:

n means 0, 1, 2, 3 or 4, where the substituents R1may be different if n is greater than 1;

R1means nitro, cyan is>if n is 2, additionally represents associated with two adjacent ring atoms optionally substituted by a bridge containing three or four members from the group containing 3 or 4 carbon atoms, 1-3 carbon atoms and 1 or 2 nitrogen atom, oxygen and/or sulphur, and this bridge together with the ring to which it is linked, may form a partially unsaturated or aromatic radical;

Y means NO2, NHOH or NHOR4;

R4means optionally substituted alkyl, alkenyl, quinil, cycloalkyl, cycloalkenyl, alkylaryl or alkoxycarbonyl;

Z denotes hydrogen, hydroxy, mercapto, cyano, nitro, halogen, C1-C6alkylsulfonyl, optionally substituted arylsulfonyl or group Za< / BR>
< / BR>
R2means hydrogen, nitro, cyano, halogen, C1-C4alkyl, C1-C4halogenated, C1-C4alkoxy, C1-C4alkylthio or C1-C4alkoxycarbonyl; R3means optionally substituted alkyl, alkenyl or quinil;

optionally substituted saturated or mono - or doubly unsaturated cycle which together with the carbon atoms may contain one to three heteroatoms as members ski radical, together with the carbon atoms may contain as members of the cycle from one to four nitrogen atoms or one or two nitrogen atom and one oxygen atom or sulfur or one oxygen atom or sulfur.

Particularly preferable for obtaining the compounds of formula I are intermediates of the formula XII, in which Y means NHOH, and Z represents a group Za.

To the preferred intermediate products of the formula XII in obtaining compounds of formula I are further those, in which Y means NO2and Z represents a group Za.

Regarding obtaining compounds of formula I in which X is NRawe should mention relating to the preferred intermediates of General formula XIII

< / BR>
where the substituents R1and R4and the index n have the meanings specified above, and the substituents W and A have the following meanings:

W stands for hydrogen, halogen or Zaand

A denotes alkyl or phenyl.

Especially preferred when the compounds of formula XIII, in which the Deputy W denotes hydrogen, chlorine, bromine or Za.

Also preferred are such compounds of formula XIII, in which mandated the are also such, in which A Deputy is phenyl.

Also preferred are such compounds of formula XIII, in which R4is hydrogen, stands or ethyl.

In addition to these preferred compounds of formula XIII, in which n denotes 0 or 1.

Among the particularly preferred compounds of formula XIII should highlight those in which the substituents and the index have the following meanings:

n means 0,

W stands for a hydrogen, chlorine, bromine or Za,

R4means hydrogen, methyl or ethyl and

A means phenyl.

The compounds of formula I may contain acidic or basic centers and form in accordance with this acid-additive products or addition products of the bases, or salts.

Acid to obtain the acid-additive products are among the other mineral acids (for example, halogenation acid, such as hydrochloric and Hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid), organic acids (e.g. formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric Antonine connection (for example, saccharin).

Grounds for obtaining products of accession grounds are amongst the oxides, hydroxides, carbonates or bicarbonates of alkali and alkaline earth metals (e.g. potassium hydroxide or sodium or potassium carbonate or sodium) or ammonium compounds (e.g. ammonium hydroxide).

When the decoding of the symbols in the above formulas partially used General concepts common to denote the following substituents:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: saturated, linear or branched hydrocarbon radicals with 1 to 4 or 10 carbon atoms, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

halogenated: linear or branched alkyl group with 1-4 carbon atoms (as specified above), and in these groups, partially or totally, the hydrogen atoms may be replaced by halogen atoms as specified above, for example, C1-C2halogenated, such as chloromethyl, dichloromethyl, trichloromethyl, vermeil, deformity, trifluoromethyl, CHLOROFORMATES, dichloromethyl, chlorodifluoromethyl, 1-foretel, 2-foretel, 2,2-dottorati, 2,2,2-triptorelin, 2-chloro-2-foretel, 2-chloro-2,2-ditto skylinee group, first of all, with 1-10 carbon atoms (as specified above), linked via a carbonyl group (-CO-) to the skeleton;

alkoxy: linear or branched alkyl group with 1-4 or 10 carbon atoms (as specified above), linked through an oxygen atom (-O-) to the skeleton;

alkoxycarbonyl: linear or branched CNS group with 1-4 carbon atoms (as specified above), linked via a carbonyl group (-CO-) to the skeleton:

alkylthio: linear or branched alkyl group with 1-4 carbon atoms (as specified above), linked to the skeleton via a sulfur atom (-S-);

optionally substituted alkyl: saturated, linear or branched hydrocarbon radicals, primarily with 1-10 carbon atoms, for example C1-C6alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2 - dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4 - methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1 - methylpropyl and 1-ethyl-2-s radicals, first of all, with 2-10 carbon atoms and a double bond in any position, for example C2-C6alkenyl, such as ethynyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1 - dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1 - methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl - 2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3 - pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4 - pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2 - butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2 - dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3 - dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-is ethyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

optionally substituted, alkenylacyl: linear or branched alkeneamine groups with 3-10 carbon atoms (as specified above), linked through an oxygen atom (-O-) to the skeleton;

quinil: linear or branched hydrocarbon group, primarily with 2-20 carbon atoms and a triple bond in any position, for example C2-C6quinil, such as ethinyl, 1-PROPYNYL, 2-PROPYNYL, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2 - PROPYNYL, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl - 2-butenyl, 1-methyl-3-butynyl, 2-methyl-3-butenyl, 3-methyl-1 - butynyl, 1,1-dimethyl-2-PROPYNYL, 1-ethyl-2-PROPYNYL, 1-hexenyl, 2 - hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 1-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-3-pentenyl, 2 - methyl-4-pentenyl, 3-methyl-1-pentenyl, 3-methyl-4-pentenyl, 4-methyl - 1-pentenyl, 4-methyl-2-pentenyl, 1,1-dimethyl-2-butinyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butinyl, 1-ethyl-3-butinyl, 2-ethyl - 3-butynyl and 1-ethyl-1-methyl-2-PROPYNYL;

optionally substituted, alkyloxy: linear or branched alkyline groups with 3-10 carbon atoms (as specified above), linked through an oxygen atom (-O-) C0 carbon atoms, for example, C3-C10(b)cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, bornyl, norbornyl, DICYCLOHEXYL, bicyclo[3,3,0]octyl, bicyclo[3,2,1]octyl, bicyclo[2,2,2]octyl or bicyclo[3,3,1]nonyl;

optionally substituted cycloalkenyl: mono - or bicyclic hydrocarbon radicals with 5-10 carbon atoms and a double bond in any position in the cycle, such as C5-C10(b)cycloalkenyl, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, borneol, norbornanyl, DICYCLOHEXYL and bicyclo[3,3,0]octenyl;

associated with two adjacent ring atoms, optionally substituted bridge containing three or four members from the group containing 3 or 4 carbon atoms, 1-3 carbon atoms and 1 or 2 nitrogen atom, oxygen and/or sulphur, and this bridge together with the ring to which it is linked, may form a partially unsaturated or aromatic radical: bridges, forming together with the ring to which they relate, for example, one of the following systems: chinoline, benzofuranyl and naphthyl;

optionally substituted, saturated or singly or doubly unsaturated cycle which together with the carbon atoms may contain as members of the cycle from the real is clopotel, cyclohexyl, cyclopent-2-enyl, cyclohex-2-enyl, 5-6-membered, saturated or unsaturated heterocycles containing one to three nitrogen atoms and/or one oxygen atom or one sulfur atom, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinone, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolinones, 4-isothiazolinone, 5-isothiazolinones, 3-pyrazolidone, 4-pyrazolidine, 5-pyrazolidone, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-diazolidinyl, 4-thiazolidine, 5-thiazolidine, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidine-3-yl, 1,2,4-oxadiazolidine-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-thiazolidin-3 - yl, 1,3,4-oxadiazolidine-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4 - thiazolidin-2-yl, 2,3-dihydrofuro-2-yl, 2,3-dihydrofuro-3-yl, 2,4 - dihydrofuro-2-yl, 2,4-dihydrofuro-3-yl, 2,3-dihydrothieno-2-yl, 2,3 - dihydrothieno-3-yl, 2,4-dehydration-2-yl, 2,4-dehydration-3-yl, 2,3 - pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,4-pyrrolin-2-yl, 2,4-pyrrolin - 3-yl, 2,3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin - 3-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazolin-4-yl, 4,5-isoxazolin - 4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin - 5-yl, 2,3-isothiazolin-3-yl, 3,4-isothiazolin-the Olin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3 - dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4 - dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol - 3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3 - dihydrooxazolo-2-yl, 2,3-dihydrooxazolo-3-yl, 2,3-dihydrooxazolo - 4-yl, 2,3-dihydrooxazolo-5-yl, 3,4-dihydrooxazolo-2-yl, 3,4 - dihydrooxazolo-3-yl, 3,4-dihydrooxazolo-4-yl, 3,4-dihydrooxazolo - 5-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxane-5 - yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrofuranyl, 3-tetrahydropyridine, 4-tetrahydropyridine, 2-tetrahydropyrimidines, 4-tetrahydropyrimidine, 5-tetrahydropyrimidine, 2-tetrahydropyranyl, 1,3,5-tetrahydropyrazin-2-yl and 1,2,4-tetrahydropyrazin-3-yl, preferably 2-tetrahydrofuranyl, 2-tetrahydrofuryl, 2-pyrrolidinyl, 3-isoxazolidine, 3-isothiazolinones, 1,3,4-oxazolidin-2-yl, 2,3-dihydrothieno-2-yl, 4,5-isoxazolin-3-yl, 3-piperidinyl, 1,3-dioxane-5-yl, 4-piperidinyl, 2-tetrahydropyranyl, 4-tetrahydropyranyl;

or optionally substituted single or dual core aromatic cyclic system, which together with the carbon atoms-can be oxygen or sulfur, either one oxygen atom or one sulfur atom, i.e., aryl radicals such as phenyl and naphthyl, preferably phenyl or 1 - or 2-naphthyl, and getaline radicals, for example, 5-cyclic heteroaromatic hydrocarbons containing from one to three nitrogen atoms and/or one oxygen atom or sulfur, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazole, 4-isothiazole, 5-isothiazole, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl, 1,2,5-triazole-3 - yl, 1,2,3-triazole-4-yl, 1,2,3-triazole-5-yl, 1,2,3-triazole-4-yl, 5-tetrazolyl, 1,2,3,4-tetrazol-5-yl and 1,2,3,4-oxadiazol-5-yl, primarily 3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl, 1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazole-2-yl;

sextillions heteroaromatic hydrocarbons containing from one to four nitrogen atoms as heteroatoms, such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazine-2-yl, 1,2,4-triazine-3-yl and 1,2 imidazenil.

The definition of "optionally substituted" with respect to alkyl, alkenyl and alkynylaryl groups means that these groups can be partially or fully halogenated (i.e., the hydrogen atoms in these groups may be partially or completely replaced by identical or different halogen atoms as stated above, preferably fluorine, chlorine and bromine, especially for fluorine and chlorine) and/or may carry one to three radicals, primarily one of the following:

C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity,

C1-C6alkylamino, di-C1-C6alkylamino, C2-C6alkenylacyl, C2-C6halogenations, C2-C6alkyloxy, C2-C6halogenaryloxy, C3-C6cycloalkyl, C3-C6cycloalkane, C3-C6cycloalkenyl, C3-C6cycloalkenyl,

or optionally substituted single or dual core aromatic cyclic system, which together with the carbon atoms may contain one to four nitrogen atoms or one or two nitrogen atom and one oxygen atom or sulfur or one oxygen atom or ser is (-S-) or amino (-NRa- can be connected with the Deputy, i.e.

aryl radicals such as phenyl and naphthyl, preferably phenyl or 1 - or 2-naphthyl, and getaline radicals, for example, 5-cyclic heteroaromatic hydrocarbons containing from one to three nitrogen atoms and/or one oxygen atom or sulfur, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazole, 4-isothiazole, 5-isothiazole, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl, 1,2,5-triazole-3 - yl, 1,2,3-triazole-4-yl, 1,2,3-triazole-5-yl, 1,2,3-triazole-4-yl, 5-tetrazolyl, 1,2,3,4-tetrazol-5-yl and 1,2,3,4-oxadiazol-5-yl, primarily 3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl, 1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazole-2-yl;

sextillions heteroaromatic hydrocarbons containing from one to four nitrogen atoms as heteroatoms, such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazine-2-yl, 1,2,4-triazinyl and 4-pyridazinyl.

The definition of "optionally substituted" in relation to the cyclic (saturated, unsaturated or aromatic) groups means that these groups can be partially or completely halogenated (i.e., the hydrogen atoms in these groups can be partially or completely be replaced by identical or different halogen atoms as stated above, preferably fluorine, chlorine and bromine, especially fluorine and chlorine) and/or may carry one to three radicals selected from among the following:

C1-C6alkyl, C1-C6halogenated, C1-C6alkoxy, C1-C6halogenoalkane, C1-C6alkylthio, C1-C6allogenicity, C1-C6alkylamino, di-C1-C6alkylamino,

C2-C6alkenylacyl, C2-C6halogenations, C2-C6alkenyl, C2-C6halogenoalkanes, C2-C6quinil, C2-C6halogenoalkanes, C2-C6alkyloxy, C2-C6halogenaryloxy, C3-C6cycloalkyl, C3-C6cycloalkane, C3-C6cycloalkenyl, C3-C6cycloalkenyl,

or optionally substituted single or dual core aromatic cyclic system is and nitrogen and one atom of oxygen or sulfur, either one oxygen atom or sulfur as members of the cycle (as described above) and which, either directly or via an oxygen atom (-O-), sulfur atom (-S-) or amino (-NRa- can be connected with the Deputy, i.e.

aryl radicals such as phenyl and naphthyl, preferably phenyl or 1 - or 2-naphthyl, and getaline radicals, for example, 5-cyclic heteroaromatic hydrocarbons containing from one to three nitrogen atoms and/or one oxygen atom or sulfur, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazole, 4-isothiazole, 5-isothiazole, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl, 1,2,5-triazole-3-yl, 1,2,3-triazole-4-yl, 1,2,3-triazole-5-yl, 1,2,3-triazole-4-yl, 5-tetrazolyl, 1,2,3,4 - tetrazol-5-yl and 1,2,3,4-oxadiazol-5-yl, primarily 3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl, 1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazole-2-yl;

sextillions heteroaromatic hydrocarbons containing from one to four nitrogen atoms as Gdinj, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazine-2-yl, 1,2,4-triazine-3-yl and 1,2,4,5-tetrazine-3-yl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl and 4-pyridazinyl.

Above when interpreting values radicals single or dual core aromatic or heteroaromatic system, in turn, can be partially or fully halogenated, i.e. the hydrogen atoms in these groups may be partially or fully replaced by halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine.

These single or dual core aromatic or heteroaromatic system along with these halogen atoms may additionally carry from one to three substituents selected from among the following:

nitro;

cyano, thiocyanato;

alkyl, first C1-C6alkyl, as defined above, preferably methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, butyl, hexyl, especially methyl or 1-methylethyl;

C1-C4halogenated, as indicated above, preferably trichloromethyl, deformity, trifluoromethyl, 2,2-dottorati, 2,2,2-triptorelin and pentafluoroethyl;

C1-C4alkoxy, preferably methoxy, ethoxy, 1 methylethoxy and 1,1-dihalogenoalkane, preferably deformations, cryptometrics and 2,2,2-cryptometrics, primarily deformations;

C1-C4alkylthio, preferably methylthio and 1 metalicity, especially methylthio;

C1-C4alkylamino as methylamino, ethylamino, propylamino, 1 methylethylamine, butylamino, 1 methylpropylamine, 2-methylpropylamine and 1,1-dimethylethylamine, preferably methylamino and 1,1-dimethylethylamine, primarily methylamino,

di-C1-C4alkylamino as N,N-dimethylamino, N,N - diethylamino, N,N-dipropylamino, N, N-di(1-methylethyl)amino, N, N-dibutylamino, N,N-di(1-methylpropyl)amino, N, N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N- (2-meth is, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably N,N - dimethylamino and N,N-diethylamino, primarily N,N-dimethylamino;

C1-C6alkylsulphonyl as methylcarbamyl, ethylcarboxyl, propylmalonic, 1-methylethylketone, butylcarbamoyl, 1 - methylpropylamine, 2-methylpropionyl, 1,1-dimethylethylamine, internabonal, 1-methylbutylamine, 2-methylbutanoyl, 3-methylbutanoyl, 1,1-dimethylpropylene, 1,2-dimethylpropylene, 2,2-dimethylpropylene, 1-ethylpropylamine, hexylcaine, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamine, 2-ethylbutylamine, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropylamine and 1-ethyl-2-methylpropionyl, preferably methylcarbamyl, ethylcarboxyl and 1,1-dimethylcarbamyl, primarily ethylcarboxyl;

C1-C6alkoxycarbonyl as methoxycarbonyl, etoxycarbonyl, prophylax-dimethylethoxysilane, pentyloxybenzoyl, 1-motivationskurser, 2-motivationskurser, 3-motivationskurser, 2,2-dimethylpropyleneurea, 1-ethylpropylamine, hexyloxymethyl, 1,1-dimethylpropanolamine, 1,2-dimethylpropyleneurea, 1-methylbenzyloxycarbonyl, 2-methylbenzyloxycarbonyl, 3-methylbenzyloxycarbonyl, 4-methylbenzyloxycarbonyl, 1,1-dimethylethoxysilane, 1,2-dimethylbutadiene, 1,3-dimethylbutylamine, 2,2-dimethylbutadiene, 2,3-dimethylbutadiene, 3,3-dimethylbutylamine, 1-ethylbutylamine, 2-ethylbutylamine, 1,1,2-trimethylammoniumphenyl, 1,2,2-trimethylammoniumphenyl, 1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropionitrile, preferably methoxycarbonyl, etoxycarbonyl and 1,1-dimethylethoxysilane primarily etoxycarbonyl;

C1-C6alkylaminocarbonyl as methylaminomethyl, ethylaminomethyl, propylaminoethyl, 1-methylaminomethyl, butylaminoethyl, 1-methylpropylamine, 2-methylpropylamine, 1,1-dimethylaminobenzoyl, intramyocardial, 1-methylbutylamine, 2-methylbutylamine, 3-methylbutylamine, 2,2-dimethylpropyleneurea, 1-ethylpropylamine, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamine, 2-ethylbutylamine, 1,1,2-trimethylaminoethyl, 1,2,2-trimethylaminoethyl, 1-ethyl-1-methylpropylamine and 1-ethyl-2-methylpropylamine, preferably methylaminoethanol and ethylaminomethyl, primarily methylaminoethanol;

di-C1-C6alkylaminocarbonyl, primarily di-C1-C4alkylaminocarbonyl as N, N-dimethylaminoethyl, N,N-diethylaminoethyl, N,N-dipropylamino, N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminoethanol, N,N-di(1-methylpropyl "aminocarbonyl, N, N-di(2-methylpropyl" aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminoethyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminomethyl, N-methyl-N-(1-methylpropyl "aminocarbonyl, N-methyl-N-(2-methylpropyl" aminocarbonyl, N-(1,1-dimethylethyl)-N - methylaminomethyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butylether)aminocarbonyl, N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N-(1-methylpropyl)-N-propylaminosulfonyl, N-(2-methylpropyl)-N-propylaminosulfonyl, N-(1,1-dimethylethyl)-N - propylaminosulfonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N- (1-methylpropyl)-aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl "aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)- aminocarbonyl, N-butyl-N-(2-methylpropyl" aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl " aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl and N-(1,1-dimethylethyl)-N-(2-methylpropyl " aminocarbonyl, preferably N,N - dimethylaminoethyl and N,N-diethylaminoethyl, primarily N,N - dimethylaminoethyl;

C1-C6alkylcarboxylic as methylcarbamoyl, ethylcarboxyl, propylgallate, 1-methylethylketoxime, butylcarbamoyl, 1-methylpropyloxy, 2-methylpropyloxy, 1,1-dimethylethylamine, interkabel, 1-methylbutylamine, 2-methylbutyrate, 3-methylbutylamine, 1,1-dimethylpropylene, 1,2-dimethylpropylene, 2,2-dimethylpropylene, 1-ethylpropylamine, hexenkessel, 1-methylphenylcarbinol, 2-methylpentylamine, 3-methylphenylacetonitrile, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamine, 2-ethylbutylamine, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy, preferably methylcarbamoyl, ethylcarboxyl and 1,1-dimethylethylamine, primarily methylcarbamoyl and 1,1-dimethylethylamine;

C1-C6alkylcarboxylic as methylcobalamine, ethylcarbodiimide, propylnitrosamine, 1 methylethylenediamine, BUTYLCARBAMATE, 1 methylpropiophenone, 2-methylpropiophenone, 1,1-dimethylethylenediamine, intelcorporation, 1 methylbutylamine, 2-methylbutylamine, 3 methylbutyronitrile, 2,2-dimethylpropanolamine, 1 ethylpropylamine, hexylcaine, 1,1-dimethylpropanolamine, 1,2-dimethylpropanolamine, 1 methylphenylethylamine, 2-methylpentylamino, 3 methylphenylethylamine, 4-methylphenylethylamine, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1 ethylbutylamine, 2-ethylbutylamine, 1,1,2-trimethyl is arbolino, preferably methylcobalamine, ethylcarbodiimide, primarily ethylcarbodiimide;

C3-C7cycloalkyl as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, preferably cyclopropyl, cyclopentyl and cyclohexyl, primarily cyclopropyl;

C3-C7cycloalkane as cyclopropylamine, cyclobutylamine, cyclopentyloxy, cyclohexyloxy, cycloheptylamine, preferably cyclopentyloxy, cyclohexyloxy, primarily cyclohexyloxy;

C3-C7cycloalkylation as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexylthio, cycloheptyl, preferably cyclohexylthio;

C3-C7cyclooctylamino as cyclopropylamino, cyclobutylamine, cyclopentylamine, cyclohexylamine, cycloheptylamine, preferably cyclopropylamino, cyclohexylamino, primarily cyclopropylamino.

Two adjacent R3radical can represent optionally substituted by fluorine, hydroxy-C1-C2alcaligenaceae, as, for example, -O-CH2-O-, -O-CF2-O-, -O-CH2CH2-O - or-O-CF2CF2-O-, or C3-C4alkylidene chain, as, for example, propylidene or butylidene.

About who can wear the radical-CR' = NOR", where the radicals R' and R" represent the following groups:

R' denotes hydrogen, cyano, alkyl (preferably C1-C6alkyl, especially C1-C4alkyl), halogenated (preferably C1-C4halogenated primarily C1-C2halogenated), alkenyl (preferably C2-C6alkenyl primarily C2-C4alkenyl), halogenoalkanes (preferably C2-C6halogenoalkanes primarily C2-C4halogenoalkanes), quinil (preferably C2-C6quinil primarily C2-C4quinil), halogenoalkanes (preferably C2-C6halogenoalkanes primarily C2-C4halogenoalkanes) and cycloalkyl (preferably C3-C8cycloalkyl primarily C3-C6cycloalkyl);

R means alkyl (preferably C1-C6alkyl, especially C1-C4alkyl), halogenated (preferably C1-C4halogenated primarily C1-C2halogenated), alkenyl (preferably C2-C6alkenyl primarily C2-C4alkenyl), halogenoalkanes (preferably C2-C6halogenoalkanes primarily C2-C4halogenoalkanes)predpochtitelno C2-C6halogenoalkanes primarily C2-C4halogenoalkanes) and cycloalkyl (preferably C3-C8cycloalkyl primarily C3-C6cycloalkyl).

Preferred compounds of formula I, taking into account their biological effectiveness are those in which n denotes 0 or 1, especially 0.

In addition to these, the preferred compounds of formula I are those in which R1represents halogen, C1-C4alkyl, C1-C2halogenated, C1-C4alkoxy or C1-C2halogenoalkane.

Also preferred compounds of formula I in which R2represents nitro, halogen, C1-C4alkyl, C1-C4halogenated, C1- C4alkoxy or C1-C4alkoxycarbonyl.

Further, among the preferred compounds of formula I should mention those in which R3represents a C1-C4alkyl or C3-C6cycloalkyl.

In addition, preferred compounds of formula I are those in which R3represents an optionally substituted single or dual core aromatic radical, kotoryy atom of oxygen or sulfur, either one oxygen atom or sulfur as members of the loop.

Especially preferred are such compounds of formula I in which R3represents phenyl or benzyl, with the phenyl radical may be partially or fully halogenated and/or may bear

from one to three radicals from the following: cyano, nitro, C1-C6alkyl, C1-C4halogenated, C1-C4alkoxy, C1-C4halogenoalkane, C1-C4alkoxy-C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkylsulphonyl, C1-C4alkoxycarbonyl, phenyl, phenoxy and phenyl-C1-C4alkoxy, and phenyl ring may be partially or fully halogenated and/or may carry one to three radicals from the following: cyano, nitro, C1-C4alkyl, C1-C2halogenated, C1-C4alkoxy, C1-C2halogenoalkane, C3-C6cycloalkyl, C1-C4alkylaryl or C1-C4alkoxycarbonyl, and/or

group CR'=NOR", in which R' means hydrogen or C1-C4alkyl, and R" represents a C1- C6alkyl, and/or

two adjacent C-atom phenyl is

In addition to these, particularly preferred compounds of formula I are those in which R3represents pyridyl or pyrimidyl, and the heteroaromatic ring may be partially or fully halogenated and/or may carry one to three radicals from the following: cyano, nitro, C1-C4alkyl, C1-C2halogenated, C1-C4alkoxy, C1-C2halogenoalkane, C3-C6cycloalkyl, C1-C4alkylaryl or C1-C4alkoxycarbonyl.

To a preferred further include such compounds of the formula I, in which R4represents hydrogen, C1-C4alkyl or C1-C2halogenated.

Also preferred are the compounds of formula I in which R5X represents methyl, ethyl, cyclopropyl, methoxy or methylamino.

Examples of most preferred compounds of the formula presented in the following tables.

Table 1

Compounds of General formula I. 1, in which R4means methyl, R5X is methyl, a Rxp corresponds to the connection specified in each row of table A.

< / BR>
Table 2

no connection, specified in each row of table A.

Table 3

Compounds of General formula I. 1, in which R4means methyl, R5X represents methoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 4

Compounds of General formula I. 1, in which R4means methyl, R5X means methylamino, a Rxp corresponds to the connection specified in each row of table A.

Table 5

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

< / BR>
Table 6

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 7

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 8

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2the 9

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 10

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 11

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 12

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 13

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 14

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means chlorine, a Rxp Samuli I. 2, in which R4means methyl, R5X is methoxy, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 16

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 17

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 18

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 19

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 20

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means bromine, a Rxp corresponds to the connection SUP> means hydrogen, R5X is methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 22

Compounds of General formula I. 1, in which R4means hydrogen, R5X is ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 23

Compounds of General formula I. 1, in which R4means hydrogen, R5X represents methoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 24

Compounds of General formula I. 1, in which R4means hydrogen, R5X means methylamino, a Rxp corresponds to the connection specified in each row of table A.

Table 25

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methyl, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 26

Compounds of General formula I. 2, in which R4means hydrogen, R5X is ethyl, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 27

Compounds of General formula I. 2, in which R

Table 28

Compounds of General formula I. 2, in which R4means hydrogen, R5X means methylamino, R2means methyl, a Rxp corresponds to the connection specified in each row of table A.

Table 29

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methyl, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 30

Compounds of General formula I. 2, in which R4means hydrogen, R5X is ethyl, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 31

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methoxy, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 32

Compounds of General formula I. 2, in which R4means hydrogen, R5X means methylamino, R2means ethyl, a Rxp corresponds to the connection specified in each row of table A.

Table 33

Compounds of General formula I. 2, in which R4

Table 34

Compounds of General formula I. 2, in which R4means hydrogen, R5X is ethyl, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 35

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methoxy, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 36

Compounds of General formula I. 2, in which R4means hydrogen, R5X means methylamino, R2means chlorine, a Rxp corresponds to the connection specified in each row of table A.

Table 37

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methyl, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 38

Compounds of General formula I. 2, in which R4means hydrogen, R5X is ethyl, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 39

Compounds of General formula I. 2, in which R4means hydrogen, R5X is methoxy, R2

Compounds of General formula I. 2, in which R4means hydrogen, R5X means methylamino, R2means bromine, a Rxp corresponds to the connection specified in each row of table A.

Table 41

Compounds of General formula I. 3 in which R5X represents methyl and the combination of the substituents R1, R2, R3and R4corresponds to the connection specified in each line of table B.

< / BR>
Table 42

Compounds of General formula I. 3 in which R5X is ethyl and the combination of the substituents R1, R2, R3and R4corresponds to the connection specified in each line of table B.

Table 43

Compounds of General formula I. 3 in which R5X is methoxy and the combination of the substituents R1, R2, R3and R4corresponds to the connection specified in each line of table B.

Table 44

Compounds of General formula I. 3 in which R5X means methylamino, and the combination of the substituents R1, R2, R3and R4corresponds to the connection specified in each line of table B.

Table 45

Compounds of General formula I. 2, in which R4means methyl, R5X means meh">

Table 46

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means cyano, a Rxp corresponds to the connection specified in each row of table A.

Table 47

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means cyano, a Rxp corresponds to the connection specified in each row of table A.

Table 48

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means cyano, a Rxp corresponds to the connection specified in each row of table A.

Table 49

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means methoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 50

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means methoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 51

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2the CA 52

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means methoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 53

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means ethoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 54

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means ethoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 55

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means ethoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 56

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means ethoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 57

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means
Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means n-propoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 59

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2means n-propoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 60

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means n-propoxy, a Rxp corresponds to the connection specified in each row of table A.

Table 61

Compounds of General formula I. 2, in which R4means methyl, R5X is methyl, R2means CF3, a Rxp corresponds to the connection specified in each row of table A.

Table 62

Compounds of General formula I. 2, in which R4means methyl, R5X is ethyl, R2means CF3, a Rxp corresponds to the connection specified in each row of table A.

Table 63

Compounds of General formula I. 2, in which R4means methyl, R5X is methoxy, R2oz is as 64

Compounds of General formula I. 2, in which R4means methyl, R5X means methylamino, R2means CF3, a Rxp corresponds to the connection specified in each row of table A.

Proposed according to the invention the compounds of formula I are suitable for combating harmful fungi and pests belonging to the classes of insects, arachnids and nematodes. They can be used for plant protection, to protect against storage pests, to protect food stocks, as well as in the field of hygiene and veterinary medicine as fungicides and means of pest control.

To insect pests include:

from the order Lepidoptera, for example, Adoxophyes orana, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Cacoecia murinana, Capua reticulana, Choristoneura fumiferana, Chilo partellus, Choristoneura occidentalis, Cirphis unipuncta, Cnaphalocrocis medinalis, Crocidolomia binotalis, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Feltia subterranea, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Manduca sexta, Malacosohyllocnistis citrella, Pieris brassicae, Plathypena scabra, Platynota stultana, Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodenia ornithogalli, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sesamia inferens, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Syllepta derogata, Synanthedon myopaeformis, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Tryporyza incertulas, Zeiraphera canadensis, in addition, Galleria mellonella and Sitotroga cerealella, Ephestia cautella, Tineola bisselliella;

from the order beetles (Coleoptera), for example, Agriotes lineatus, Agriotes obscurus, Anthonomus grandis, Anthonomus pomorum, Apion vorax, Atomaria linearis, Blastophagus piniperda, Cassida nebulosa, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Dendroctonus refipennis, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllopertha horticola, Phyllophaga sp., Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Psylliodes napi, Scolytus intricatus, Sitona lineatus, in addition, Bruchus rufirmanus, Bruchus pisorum, Bruchus lentis, Sitophilus granaria, Lasioderma serricorne, Oryzaephilus surinamensis, Rhyzopertha dominica, Sitophilus oryzae, Tribolium castaneum, Trogoderma granarium, Zabrotes subfasciatus;

from the order Diptera, for example, Anastrepha ludens, Ceratitis capitata, Contarinia sorghicola, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia coarctata, Delia band, Hydrellia griseola, Hylemyia platura, Liriomyza sativae, Liriomyza trifoaludosa, in addition, Aedes aegypti, Aedes vexans, Anopheles maculipennis, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hypoderma lineata, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Musca domestica, Muscina stabulans, Oestrus ovis, Tabanus bovinus, Simulium damnosum;

from the order of Puzanova (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Haplothrips tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci;

from the order Hymenoptera (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Iridomyrmes humilis, Iridomyrmex purpureus, Monomorium pharaonis, Solenopsis geminata, Solenolsis invicta, Solenopsis richteri;

detachment of these bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus hesperus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor;

from the order Orthoptera Robotnik (Homoptera), for example, Acyrthosiphon onobrychis, Acyrthosiphon pisum, Adelges laricis, Aonidiella aurantii, Aphidula nasturtii, Aphis fabae, Aphis gossypii, Aphis pomi, Aulacorthum solani, Bemisia tabaci, Brachycaudus cardui, Brevicoryne brassicae, Dalbulus maidis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosoma lanigerum, Laodelphax striatella, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Perkinsiella saccharicida, Phorodon humuli, Planococcus citri, Psylla mali, Psylla piri, Psylla pyricol, Quadraspidiotuporariorum, Viteus vitifolii;

from a squadron of termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Macrotermes subhyalinus, Odontotermes formosanus, Reticulitermes lucifugus, Termes natalensis;

from the order Orthoptera (Orthoptera), for example, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Schistocerca gregaria, in addition, Acheta domestica, Blatta orientalis, Blattella germanica, Periplaneta americana;

from the class arachnids (Arachnoidea), such as plant mites, such as Aculops lycopersicae, Aculops pelekassi, Aculus schlechtendali, Brevipalpus phoenicis, Bryobia praetiosa, Eotetranychus carpini, Eutetranychus banksii, Eriophyes sheldoni, Oligonychus pratensis, Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Tarsonemus pallidus, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus urticae, pasture mites, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, lxodes ricinus, lxodes rubicundus, Ornithodorus moubata, Octobius megnini, Rhipicephalus appendiculatus and Rhipicephalus evertsi and clamp zooparasitic, such as Dermanyssus gallinae, Psoroptes ovis and Sarcoptes scabiei;

from the class of the nematodes, for example root-knot nematodes such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, such as Globodera pallida, Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, migratory endoparasites and temporary endoparasites-nematodes, for example Helrmis, Scutellonema bradys, Tylenchulus semipenetrans, stem and leaf nematodes, such as Anguina tritici, Aphelenchoides besseyi, Ditylenchus angustus, Ditylenchus dipsaci, the vector is a viral infection, such as Longidorus spp., Trichodorus christei, Trichodorus viruliferus, Xiphinema index, Xiphinema mediterraneum.

The compounds of formula I can be used individually, in the form of their compositions or made from them for the use of forms, for example in the form intended for direct spraying of solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, products for dusting, dusting, granular materials, and the treatment is carried out by various methods, such as spraying, treatment in the form of mists, dusting, dusting or watering. Methods and forms of application depend entirely on the purpose of the application, but in all cases must be ensured to the maximum fine and uniform distribution of the active substances according to the invention.

As fungicides compounds of formula I possess partially systemic action. They can be used as fungicides for the processing of the leaves as soil fungicides against a broad spectrum of phytopathogenic fungi, primarily related to the class Ascomyceten, Deuteromyceten, Phycomyceten and Basidiomyceten.

The compounds of formula I are especially suitable for dealing with the following plant diseases: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on Cucurbitaceae, Podosphaera leucotricha on apples, Uncinula necator on grape vines, Puccinia species on cereals, Rhizoctonia species on cotton and turf, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (grey mould) on strawberries, grape vines, Cercospora arachidicola on groundnut, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium species and Verticillium on different crops, Plasmopara viticola on grape vines, Alternaria species on vegetables and fruit crops.

The new compounds can also be used for protecting materials, in particular wood, for example, from this pathogen, as Paecilomyces variotii.

They can be used for the preparation of conventional compositions, such as RA and consequently from the target application, but in any case, it should be ensured as much as possible thin and uniform distribution of active ingredients in the composition.

The compositions are prepared by known methods, for example by dilution of the active compounds using solvents and/or by the addition of fillers, optionally using emulsifiers and dispersants, and in the case of use as diluent water may also be used other organic solvents that serve as auxiliary agents solubility.

As auxiliary agents solubility for these purposes can serve mainly the following:

- solvents, such as aromatic hydrocarbons (e.g. xylene), chlorinated aromatic hydrocarbons (e.g. chlorobenzene), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water;

- fillers such as mineral flour (for instance, kaolins, alumina, talc, chalk), synthetic mineral flour (for example, finely dispersed silicic acid, silicates);

- emulsifiers such as nonionic and anionic emulgatoren, such as exhaust ligninolytic liquor and methylcellulose.

As surface-active substances can be considered salts of alkali and alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example ligninsulfonate acid, phenolsulfonic acid, naphtalenesulfonic acid and dibutylaminoethanol acid, and of fatty acids, alkyl - and alkylarylsulfonates, alkyl sulphates, sulphates lauric ester and fatty alcohols, and salts of sulfated hexa-, hepta - and octadecanol, glycol ether of fatty alcohols, the reaction products of condensation of sulfonated naphthalene and its derivatives with formaldehyde, reaction products of condensation of naphthalene, respectively naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneglycol esters, ethoxylated isooctyl-, octyl - or Nonylphenol, polyglycolide esters of alkylphenol and tributylamine, alkylacrylate esters of polyalcohol, isotridecyl alcohol, condensates of ethylene oxide fatty alcohols, ethoxylated castor oil, easy polyoxyethylene - or Polyoxypropylenediamine ester, acetate ester of lauric alcohol and polyglycols, esters of sorbitol, otrabatawawrzih concentrates, dispersions, pastes, wettable powders or dispersible in water granules by adding water. To obtain emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting, adhesives, dispersants or emulsifiers. Along with these active substances can also be produced concentrates, including wetting, adhesives, dispersants or emulsifiers and are suitable for dilution with water.

Powder preparations, preparations for dusting and dusting can be produced by mixing or joint grinding of active substances with any solid filler.

The granules such as pellets in the shell, impregnated granulates and homogeneous granulates can be obtained by binding of active substances with solid fillers. Such solid fillers can serve as mineral lands, in particular silica gel, silicic acid, diatomaceous earth, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as Sul grain, flour made from tree bark, wood flour and flour from a nutshell, cellulose powders or other solid fillers. The concentration of active substance in ready-for-use compositions may vary within wide limits.

Generally, the compositions contain the active substance in the range from 0.0001 to 95 wt.%. Compositions containing the active substance more than 95 wt.% can be successfully applied in the so-called method of ultra-low volume (Ultra-Low-Volume = ULV: anhydrous spraying pesticides at the rate of solution flow rate of active substances just 0.1-0.6 l/ha using compressed air as a dispersant), and the active substance can be used even without supplements.

For use as fungicides are recommended concentration of active ingredient is from 0.01 to 95 wt.%, preferably from 0.5 to 90 wt.%. For use as insecticides recommended composition with the concentration of the active substance from 0.0001 to 10 wt.%, preferably from 0.01 to 1 wt.%. Active ingredients when applied usually with a degree of purity (according to NMR spectrum) from 90% to 100%, preferably from 95% to 100%.

The examples described above Ref. parts N-methyl - pyrrolidone, designed for use in the form of tiny droplets.

II. A solution of 20 wt. parts of the compounds of formula I according to the invention in a mixture of 80 wt. parts of alkylated benzene, 10 wt. parts of the product of the merger 8-10 moles of ethylene oxide to 1 pray N-mono-ethanolamide oleic acid, 5 wt. parts of the calcium salt dodecylbenzenesulfonic acid, 5 wt. parts of the product of the joining of 40 moles of ethylene oxide to 1 pray castor oil; after a fine and uniform distribution of the composition in water get the corresponding variance.

III. A solution of 20 wt. parts of the compounds of formula I according to the invention in a mixture of 40 wt. parts of cyclohexanone, 30 wt. parts of Isobutanol, 20 wt. parts of the product of the joining of 7 moles of ethylene oxide to 1 pray isooctylphenol and 10 wt. parts of the product of the joining of 40 moles of ethylene oxide to 1 pray castor oil; after a fine and uniform distribution of the composition in water get the corresponding variance.

IV. Aqueous dispersion of 20 wt. parts of the compounds of formula I according to the invention in a mixture of 25 wt. parts of cyclohexanone, 65 wt. parts of the fraction of fuel oil with a boiling point 210-280oC, the oil; after a fine and uniform distribution of the composition in water get the corresponding variance.

V. Crushed in a hammer mill, a mixture of 20 wt. parts of the compounds of formula I according to the invention, 3 wt. parts of the sodium salt of diisobutylamine--sulfonic acid, 17 wt. parts of the sodium salt ligninsulfonate acid from spent sulfite liquor and 60 wt. parts of powdered silica gel; after a fine and uniform distribution of the mixture in water to obtain a solution for spraying.

VI. Homogeneous mixture of 3 wt. parts of the compounds of formula I according to the invention and 97 wt. parts of fine kaolin; this drug for dusting contains 3 wt.% the active substance.

VII. Homogeneous mixture of 30 wt. parts of the compounds of formula I according to the invention, 92 wt. parts of powdered silica gel and 8 wt. parts of paraffin oil, which is sprayed on the surface of this silica gel; this method of preparing the active substance acquires a good adhesive ability.

VIII. A stable aqueous dispersion of 40 wt. parts of the compounds of formula I according to the invention, 10 wt. parts of the sodium salt to the th can be further diluted.

IX. A stable oily dispersion of 20 wt. parts of the compounds of formula I according to the invention, 2 wt. parts of the calcium salt dodecylbenzenesulfonic acid, 8 wt. parts polyglycolic ether fatty alcohol, 2 wt. parts of the sodium salt of a condensate phenolsulfonic acid-urea-formaldehyde and 68 wt. parts of a paraffinic mineral oil.

X. Crushed in a hammer mill, a mixture of 10 wt. parts of the compounds of formula I according to the invention, 4 wt. parts of the sodium salt of diisobutylamine--sulfonic acid, 20 wt. parts of the sodium salt ligninsulfonate acid from spent sulfite liquor, 38 wt. parts of silica gel and 38 wt. parts of kaolin. After a fine and uniform distribution of the mixture in 10000 wt. the parts of water to obtain a solution for spraying, containing 0.1 wt.% the active substance.

The principle of using compounds of formula I consists in the fact that the mushrooms or the seeds, plants, materials or soil to be protected from damage by fungi, process fungicide effective amount of active substances. Such processing is carried out before or after infection of the materials, plants or seeds by the fungi. Consumption rates depending on what effect I want Pian norms of consumption of the active substance is usually, from 0.001 to 50 g, preferably 0.01 to 10 g per kilogram of seed. For pest control in conditions of open ground active substance is applied in a quantity of 0.02 to 10, preferably 0.1 to 2.0 kg/ha.

The compounds of formula I, individually or in combination with herbicides or fungicides can also be used for co-processing in a mixture with other crop protection agents, for example with growth regulators or means in the fight against pests or bacteria. You might be interested in then the possibility of mixing with fertilizers or with solutions of mineral salts, which are intended to compensate the lack of nutrients and trace elements.

Plant protection products and fertilizers can be added to the funds according to the invention in a ratio by weight of from 1:10 to 10:1, if necessary, such additives may be introduced directly before processing (vessel for mixing). When mixed with fungicides or insecticides in many cases come to broaden the spectrum of fungicidal action.

Below is a list of fungicides, in conjunction with which can be applied compounds according to the invention, this list is for pojam include:

sulfur, dithiocarbamates and their derivatives, such as peridomiciliary, zinc dimethyldithiocarbamate, ethylenebisdithiocarbamate zinc, ethylenebisdithiocarbamate manganese, manganese-zinc-ethylenediaminediacetic, tetramethylthiourea, ammonia complex of zinc(N,N-ethylenebisdithiocarbamate), ammonia complex of zinc(N,N'-propyltrimethylammonium), zinc(N,N'-propyltrimethylammonium), N,N'-polypropylenes(thiocarbamoyl-yl)disulphide;

nitro-derivatives, such as dinitro(1-methylheptan)phenylketone, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6 - dinitrobenzophenone, diisopropyl ether 5-nitroisophthalic acid;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O, O-diethylthiophosphoryl, 5-amino-1-- [bis(dimethylamino)phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyan-1,4-dicyandiamide, 2-thio-1,3-dithiolo- - [4,5-b]cinoxacin, methyl ester 1-(butylcarbamoyl)-2-benzimidazolecarbamic acid, 2-methoxycarbonylaminophenyl, 2-(furyl-(2))-benzimidazole, 2-(thiazolyl-(4))benzimidazole, N-(1,1,2,2 - tetrachloroethylthio)tetrahydrophthalate, N-trichloromethylpyridine, N-trikhlormyetilsilanye, diamid N-dilasa, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazone)-3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline, according to its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide, anilide 2-methyl-5,6-dihydro-4H-Piran-3-carboxylic acid, anilide 2-methylfuran-3-carboxylic acid, anilide 2.5-dimethylfuran-3-carboxylic acid, anilide 2,4,5-trimethylphenyl-3-carboxylic acid, cyclohexylamine 2.5-dimethylfuran-3-carboxylic acid amide N-cyclohexyl-N - methoxy-2,5-dimethylfuran-3-carboxylic acid, anilide 2 - methylbenzoic acid, anilide 2-iodobenzoyl acid, N-formyl-N - morpholine-2,2,2-trichloroacetyl, piperazine-1,4-diylbis-1-(2,2,2 - trichlorethyl)formamid, 1-(3,4-dichloraniline)-1-formylamino-2,2,2 - trichloroethane, 2,6-dimethyl-N-tredecillion, respectively, its salts, 2,6-dimethyl-N-cyclododecyl, respectively, its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl] -CIS-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl] piperidine, 1-[2-(2,4 - dichlorophenyl)-4-ethyl-1,3-dioxolane-2-ileti] -1H-1,2,4-triazole, 1- [2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolane-2-ileti] -1H-1,2,4 - triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxy)-N'- imidazolidine, 1-(4-chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4 - Tr is midemeanor, 5-butyl-2-dimethylamino-4-hydroxy-6 - methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3 - etoxycarbonyl-2-touraid)benzene, 1,2-bis(3-methoxycarbonyl-2 - touraid)benzene,

and various fungicides, such as dodecylguanidine, 3-[3-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N-(2,6-dimetilfenil)-N-furoyl(2)alanine, methyl ester of DL-N-(2,6-dimetilfenil)-N-(2'-methoxyacetyl)alanine, N-(2,6-dimetilfenil)-N - chloroacetyl-DL-2-aminobutyrate, methyl ester of DL-N-(2,6-dimetilfenil)-N-(phenylacetyl)alanine, 5-methyl-5 - vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-[3,5-dichlorophenyl (5-methyl-5-methoxymethyl)]-1,3-oxazolidin-2,4-dione, 3-(3,5-dichlorophenyl)-1 - isopropylcarbodiimide, imide N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane - 1,2-dicarboxylic acid, 2-cyano-[N-(acylaminoalkyl)-2-methoxyimino] ndimethylacetamide, 1-[2-(2,4-dichlorophenyl)pentyl] -1H-1,2,4-triazole, 2,4-debtor- - (1H-1,2,4 - triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4 - triptoreline)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-forfinal)methylsilyl)methyl)-1H-1,2,4-triazole.

Examples of the synthesis of

See the following examples of synthesis of recommendations were used, with appropriate modification of the original with the emnd table In specifying physical characteristics.

1. Methyl ester of N-(2-(N'-(o-chlorophenyl)-5'-methylthiazolyl-3' -oxymethyl)phenyl)-N-methoxycarbonyl acid (table V, N 11)

A mixture of 3.3 g (purity about 80%; 10 mmol) of methyl ester of N-(2-bromomethylphenyl)-N-methoxycarbonyl acid (WO 93/15046), 2.1 g (10 mmol) N-(o-chlorophenyl)-3-hydroxy-5-methylthiazole and 2 g (15 mmol) of K2CO3in 20 ml of DMF is stirred overnight at room temperature. Then the reaction mixture was diluted with water and the aqueous phase three times extracted with methyl tert-butyl ether. The combined organic phases are extracted with water, dried over MgSO4and concentrate. The residue is purified by column chromatography using mixtures of cyclohexane-ethyl ester of acetic acid. This way obtain 1.1 g (27%) indicated in the title compound as a yellow oil.

1H-NMR (CDCl3; frequent./million): to 7.7 (m, 1H, phenyl); at 7.55 (m, 1H, phenyl); and 7.4 (m, 6H, phenyl); to 5.35 (s, 2H, OCH2); 3,72, of 3.77 (2s, 3H, 2OCH3); to 2.25 (s, 3H, CH3).

2. Methyl ester of N-(2-(N'-phenyl-5'-chlorothiazole-3'- oxymethyl)phenyl)-N-methoxycarbonyl acid (table B, N 15)

A mixture of 3.3 g (purity about 80%; 10 mmol) of methyl ester of N-(2-bromomethylphenyl)-N-methoxycarbonyl acid (WO 93/one night at room temperature. Then the reaction mixture was diluted with water and the aqueous phase three times extracted with methyl tert-butyl ether. The combined organic phases are washed with water, dried over MgSO4and concentrate. The residue is purified by column chromatography using mixtures of cyclohexane-acetic ether. This way obtain 2.7 g (69%) indicated in the title compound as a yellow oil.

3. Methyl ester of N-(2-(N'-pyridyl-2"-triazolyl - 3'-oxymethyl)phenyl)-N-methoxycarbonyl acid (table B, N 40)

A mixture of 2.7 g (purity about 80%; 8 mmol) of methyl ester of N-(2-bromomethylphenyl)-N-methoxycarbonyl acid (WO 93/15046), 1.7 g (8 mmol) of N-(pyridyl-2')-3 - hydroxytriazolam and 1.7 g (12 mmol) of K2CO3in 20 ml of DMF is stirred overnight at room temperature. Then the reaction mixture was diluted with water and the aqueous phase three times extracted with methyl tert-butyl ether. The combined organic phases are extracted with water, dried over MgSO4and concentrate. The residue is purified by column chromatography using mixtures of cyclohexane-acetic ether. This way obtain 1.4 g (49%) indicated in the title compound as a colourless solid (tPL89oC).

1H-NMR (CDCl5 (s, 2H, OCH2); 3,8, 4,75 (2s, 3H, 2OCH3).

Examples of research action against harmful fungi

Fungicidal efficacy of the compounds of the formula I were confirmed during the following experiments.

Of the active ingredients to prepare a 20% emulsion in a mixture consisting of 70 wt.% cyclohexanone, 20% by weight NekanilLN (LutensolAP6, wetting agent with emulsifying and dispersing action based on ethoxylated ALKYLPHENOLS) and 10 wt.% EmulphorEL (EmulanEL, emulsifier based on ethoxylated fatty alcohols), and then the emulsion was diluted with water to the desired concentration.

Action against Puccinia recondita

Leaves of wheat seedlings (cultivar "Kanzier") apilevel spores of brown rust (Puccinia recondita). The thus treated plants were incubated for 24 h at 20-22oC and relative humidity of 90-95%, after which the treated water composition of active substances (63 frequent./million active substance). After 8 days at 20-22oC and relative humidity of 65-70% and determined the degree of development of fungi. The evaluation was made visually.

In this test, the degree of destruction of plants, processing the deposits, treated with compound known from WO 93/15046 (table 7, example 8) was up 25%. The extent of the lesion untreated plants was 70%.

In another similar experiment, the degree of the damage of the plants treated with 250 ppm million connections NN 1, 2, 4-10, 12, 13, 15, 17-19, 21, 23-26, 28-31, 33, 37, 38, 42, 43 and 45 according to the invention was 10% or less, whereas the corresponding figure in plants treated with compound known from WO 93/15046 (table 7, example 8) was up 25%. The extent of the lesion untreated plants was 70%.

Action against Botrytis cinerea (grey mould)

Seedlings of capsicum (cultivar "Neusiedler Ideal Elite") in stage 4-5 leaves intensively sprayed with the composition of active ingredients (the amount of 500 ppm million). After drying, the plants were sprayed with a suspension of conidia of the fungus Botrytis cinerea, and then kept for 5 days at a temperature of 22-24oC under conditions of high humidity. Evaluation of the results was made visually.

In this test, the plants treated with compound No. 2 according to the invention, were amazed by 5%, whereas the degree of the damage to plants treated with compound known from WO-A 93/15046 (table 2, N I/270) accounted for up to 80%. This indicator untreated plants is ryskovaly composition of active substances (used amount of 250 ppm million). After 24 h, the plants were sprayed with an aqueous suspension of spores of the fungus Pyricularia oryzae, after which they kept for 6 days at a temperature of 22-24oC and at a relative humidity of 95-99%. Evaluation of the results was made visually.

In this experiment the degree of the damage to plants treated with compound No. 2 according to the invention, was 3%, while this rate in plants treated is known from WO-A 93/15046 compound (table 2, N I/270), reached 25%; the degree of the damage of untreated plants was 70%.

In a similar experiment, the degree of the damage of the plants treated with 250 frequent. /million connections 2, 6-8, 13, 15, 17-19, 21, 24-38 and 42-45 according to the invention, was 5% or less, whereas the corresponding figure in plants treated is known from WO 93/15046 compound (table 2, N I/270), reached 25%; the degree of the damage of untreated plants was 70%.

Action against Fusarium culmorum

Primary leaves of wheat seedlings (cultivar "Kanzler") was intensively sprayed composition of active substances (used amount of 500 ppm million). The following day plants were infected by a spore suspension of Fusarium culmorum. Then the thus treated plants were incubated for 6 days at a temperature of 22-24oC Epen destruction of plants, treated with compound No. 2 according to the invention, was 5%, while this rate in plants treated is known from WO-A 93/15046 compound (table 2, N I/270), reached 25%; the degree of the damage of untreated plants was 60%.

Examples of research activities against pests

The effectiveness of compounds of General formula I in relation to the pest was confirmed in the course of conducting the following experiments.

Of the active ingredients to prepare

a) 0.1% solution in acetone or

b) a 10% emulsion in a mixture of 70 wt. % of cyclohexanone, 20% by weight NekanilLN (LutensolAP6, wetting agent with emulsifying and dispersant action based on ethoxylated ALKYLPHENOLS) and 10 wt.% EmulphorEL (EmulanEL, emulsifier based on ethoxylated fatty alcohols) and diluted to the desired concentration of acetone in the case (a), respectively, with water in case b).

After completion of the experiments were determined, respectively, the lowest concentration at which the compounds according to the invention in comparison with the untreated control was still 80-100% inhibition or destruction of pests (threshold effect, the corresponding R1means C1-C4alkyl, halogen;

R2means hydrogen, halogen, C1-C4alkyl, C1-C4halogenated, C1-C4alkoxygroup;

R3means C1-C4alkyl, phenyl, unsubstituted or substituted by 1 to 2 halogen atoms, C1-C6the alkyl, C1-C4haloalkyl, nitro, C1-C4alkoxyl, C1-C4haloalkoxy, phenyl or fenoxaprop; 2-pyridyl, unsubstituted or substituted C1-C4haloalkyl, 2-pyrazinyl or pyridyl substituted by halogen;

R4means hydrogen or C1-C4alkyl;

R5means C1-C4alkyl;

X represents oxygen or NH;

n = 0 or 1.

2. Intermediates of formula XII

< / BR>
where R1, R2, R3and n are specified in paragraph 1 values;

Y represents NO2or NHOR4where R4has the meaning specified in paragraph 1.

3. Means of combating harmful fungi, containing solid or liquid filler and a compound of General formula I on p. 1.

 

Same patents:
The invention relates to pharmaceutical industry, and in particular to a method for producing an antiemetic - ondansetron

The invention relates to pharmaceutical industry

The invention relates to a new derivative of 4-oxo-1,4-dihydropyrimidin, specifically: 2,6-diethyl-5-phenyl-1(5,6-dimethylbenzimidazolyl-1)-4-oxo-1,4-dihydropyrimidine (I) having immunosuppressive activity, which can find application in medicine

The invention relates to new 4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridine F.-ly (I), where Y is CH or N; R1-H, halogen, CF3; R2-H, halogen, (C3- C4)alkyl or (C1- C4)alkoxy; R3and R4- H or (C1- C3)alkyl; X represents: (a) (C3- C6)alkyl, (C3- C6)alkoxy or (C1- C4)alkoxycarbonyl(C3- C6)alkoxy, (b), (C3- C7)cycloalkyl or c) Deputy chosen from the group comprising phenyl, phenoxybenzyl, their salts, solvate or Quaternary ammonium salts

The invention relates to new 4-substituted piperidine derivative that is related to ones antagonists neirokinina 2 (NK), which can be used, for example, in the treatment of diseases such as asthma, and method of production thereof

The invention relates to 2-[(dihydro)pyrazolyl-3'-oxymethylene] anilides formula I

< / BR>
in whichmeans simple or double bond, and the index and the substituents have the following meanings:

n means 0, 1 or 2;

m means 0, 1 or 2 and the substituents R2may be different if m is greater than 1;

X represents a direct bond, O or NRa;

Rameans hydrogen;

R1means halogen or C1-C4alkyl, or, if n is 2, represents optionally associated with two adjacent ring atoms of the hydrocarbon bridge containing 3 or 4 carbon atoms;

R2means nitro, halogen, C1-C4alkyl, C1-C4halogenated or1-C4alkoxycarbonyl;

R3means optionally substituted alkyl, optionally substituted saturated cycle or optionally substituted single or dual core aromatic radical, which together with the carbon atoms may contain as members of the cycle from one to four nitrogen atoms;

R4means hydrogen, optionally substituted alkyl;

The invention relates to new nitrogen-containing heterocyclic compounds possessing biological activity, in particular fungicidal activity, and more particularly to a derivative triazolyl, the way they are received and fungicidal tool
Up!