UA67734C2 - 1-arylpyrazole-3-thiocarboxamide derivatives having pesticide properties - Google Patents

Abstract

The invention relates to 1-arylpyra-zole-3-thiocarboxamide derivatives of formula (I), wherein R1, R2, R3, R4, R5, N, Z and n are as defined in the description, and to their use as insecticides.

Description

Description of the invention

The present invention relates to new 3-thiocarboxamide derivatives of 1-arylpyrazoles and their derivatives. The invention, 2 in addition, refers to compositions based on the specified compounds and methods in which the specified compounds are used, intended for the control of arthropod pests, in particular, to the use of the specified compounds or compositions in methods used in agriculture, in particular as pesticides, for the control of arthropod pests, especially insects, with the help of a systemic action.

Description of the Prior Art 10 Control of insects, nematodes or helminths using 1-arylpyrazoles is described in international patent publications Mo93/06089 (and the corresponding US patent Mo5451596), UUMO94/21606 and UUO87/03781, as well as in European patent publications MoMo0295117, 659745 , 679650, 201852 and 412849, German patents

MoOE19511269 and US patent Mo5232940.

OBJECTIVES AND BRIEF DESCRIPTION OF THE INVENTION An object of the present invention is to provide novel compounds of the 1-arylpyrazole family that are pesticides, together with methods for their preparation.

A second object of the present invention is to provide pesticidal compositions and methods of use, as pesticides having pesticidal properties, of pyrazole compounds against arthropods, especially insects, in particular, in relation to agricultural or horticultural crops, in forestry, veterinary medicine or animal husbandry, or in public health care.

A third object of the present invention is to provide highly active compounds with a broad spectrum of pesticidal activity, as well as compounds with selective specific activity, for example, aphidicidal, miticidal, insecticidal, foliar, soil-based, systemic, anti-feeding, or pesticidal. action provided during seed processing. c 25 A fourth object of the present invention is to provide compounds with significantly enhanced and more rapid action, particularly against insects and, more specifically, against insects in the larval stage.

A fifth objective of the present invention is to provide compounds with significantly improved (faster and more significant) penetration into pest species when topically applied, and thus to provide enhanced penetration of the compound to sites of pesticidal action within the pest. in 30 These and other objects of the invention will become apparent from the further description of this invention. The invention will fully or partially satisfy these objectives.

The invention offers 1-arylpyrazoles with insecticidal properties, which have the general formula (1): in - era He 7 7

In, vit « to. - with ;" FO where:

K is H or halogen; (o) each of K. and Ku, which are the same or different, is H, halogen or alkyl; -1 Kz is a halogen, haloalkyl, haloalkoxy or K 105(O)24; mainly. Kz is halogen, haloalkyl or haloalkyl; - and Kb is alkyl, haloalkyl, alkenyl and alkynyl; or a cycloalkyl ring containing from 3 to 5 to 50 hydrocarbon atoms; preferably, K5 is alkyl; 7 represents hydrogen, halogen, alkyl, formyl, -C(O) alkyl, haloalkyl; alkenyl, hydrazino,

I» alkoxycarbonyl, alkylthiocarbonyl, alkoxyalkylidenamino, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl; or, preferably, 7 represents: amino, KeMH- or KURaM-; each of the radicals Kv, K7 and Kv, which can be the same or different, represent alkyl - (0) p-, formyl having from 3 to 6 hydrocarbon atoms, alkynyl, alkoxycarbonyl alkylthiocarbonyl or aryl; or alkyl, o having from C to b alkenyl atoms or -C(O)-alkyl, in which the alkyl and alkenyl parts are, optionally, substituted by one or more Co radicals; ko or radicals K;7 and Ka are combined in such a way that together they form a divalent radical containing from 4 to b hydrocarbon atoms in the chain, and this divalent radical is alkylene, 60 alkyleneoxyalkylene or alkyleneaminoalkylene, preferably with the formation of morpholine, pyrrolidine , piperidine or piperazine cycle;

Co is cyano, niro, alkoxy, haloalkoxy, K 405(0)4-, -C(O)-alkyl, alkoxycarbonyl aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, -СО2Н, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or diaminosulsronyl; 65 Ko represents lower alkyl or lower haloalkyl; t,p,p and 4 are equal to 0,1 or 2;

M represents - C-halogen, C-CH z, C-SNOR, C-СНоСИ, С-МО" or M; and their salts, which have a pesticidal effect. The term "pesticidal salts" means salts whose anions and cations are known and generally accepted in technology for the formation of salts acceptable as pesticides. Preferably, such salts are soluble in water. Suitable addition salts of acids formed from compounds of formula (1) containing an amino group include salts with inorganic acids, for example, hydrochlorides, phosphates, sulfates and nitrates, and salts with organic acids, for example, acetates. Suitable alkali salts formed from compounds of formula (1) containing a carboxylic acid group include alkali metal salts (eg sodium or potassium), ammonium salts and organic amine salts (eg diethanolamine or morpholine). 70 Detailed description of the invention

Unless otherwise indicated, alkyl, alkoxy, and alkylthio groups contain from one to six (preferably from one to four) hydrocarbon atoms. Alkenyl and alkynyl groups contain from two to six (preferably from two to four) hydrocarbon atoms, in this invention some terms are used in the following specific meaning.

The term "aminocarbonyl" means a carbamoyl radical, that is, a radical of the formula -С(О)МН». Similarly, the term "alkylaminocarbonyl" means an alkylcarbamoyl radical, that is, a radical of the formula -C(O)MH-alkyl; and the term "dialkylaminocarbonyl" means a dialkylcarbamoyl radical, that is, a radical of the formula -C(O)M(alkyl)", in which the alkyl residues can be the same or different. The term "aminosulfonyl" means a sulfamoyl radical, i.e., -ZOO 2 MNo. Similarly, the term "alkylaminosulfonyl" means an alkylsulfamoyl radical, that is, a radical of the formula -505MH-alkyl; while the term "dialkylaminosulfonyl" means a dialkylsulfamoyl radical having the formula -ZOOM(alkyl)", in which the alkyl residues may be the same or different.

The term "halogen" before the name of the radical means that this radical is partially or fully halogenated, that is, in other words, substituted by BE, SI, Bg or y atoms in any combination, preferably by E or SI atoms. high school

The term "halogen" means E, Cl, Bg or 5). In the event that the name of any substitute is repeated, it retains the same meaning, unless otherwise indicated. The term "aroyl" means a carbonylaromatic radical, and) that is, an aryl-C(0)- radical, which is preferably benzoyl, optionally substituted by one or more alkyl or halogen groups.

A particularly preferred class of compounds of formula (1) includes those where: "g zo EK" represents EK, SI, Bg or H;

E" and Ka represent H; at

Kz represents -SEz, -OSEz, -"SNE", -(O)tSE»z, -SESI", -SE»SI, -OSE»SI, -OSESI", SI, Vg or E; uh-

Kb is methyl or ethyl; 7 represents H, halogen (E, CI, Bg), C 1-C3-alkyl, C--C3-haloalkyl, C--C3-alkenyl; or amino, -MNK; or in zv MK Kv, where each of the radicals KeK" and Kv, which are the same or different, represents C 4-C3-alkyl, C3-alkenyl "o or -C(O) alkyl, in which the alkyl and alkenyl parts are unsubstituted or substituted by cyano, alkoxy, alkyl-5(O)p-, nitro, alkoxycarbonyl, -C(O)alkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, -СО5Н, hydroxy or halogen. (E, SI, Bg) and

M represents SSI, SE, SVg or M. "

The next, particularly preferred class of compounds consists of those in which: in c Ku is SI or HV;

E" and KE; are H; ;" Kz represents -SEz, -"OSE" or SI;

Co represents methyl or ethyl; 7 represents H, halogen (E, CI, Bg), C 1-C3-alkyl, C--C3-haloalkyl, Co-C3-alkenyl; or. amino, - MNK; or

Ge" -MA7Ka, where each of the radicals Kb, K; and Kv, which are the same or different, is C 1-C3-alkyl, C3-alkenyl or -C(O)alkyl, in which the alkyl and alkenyl parts are unsubstituted or substituted by cyano, alkoxy,

Sh- alkyl-5(O) p-, nitro, alkoxycarbonyl, -C(O)alkyl, aminocarbonyl, alkylaminocarbonyl, -I dialkylaminocarbonyl -СО5Н, hydroxy or halogen (E C, Bg); and

M represents SSI, SVg or M. o The next especially preferred class of sa|Keg consists of those in which: и» Ku represents SI or HV;

E" and KE; are H;

Kz represents -SEz, -OSE»z or SI; 5B Kb is optionally halogenated methyl or ethyl; 7 is H or amino; and (F) M represents SSI, SVg or M. ka Y another especially preferred class of so|)Keg are those of them in which:

Ku represents SI or HV; 60 E" and KE; are H;

Kz represents -SEz, -OSE" or SI;

Kb is methyl or ethyl; 7 is H or amino; and

M represents SSI, SVg or M. 65 For the above-mentioned preferred compounds there are optimal combinations of substituent groups.

Preferred phenyl groups or pyridyl groups containing in formula (1) radicals K.-K, and

M, there are groups: 2,6-dichloro-4-rifluoromethylphenyl; 2,6-dichloro-4-trifluoromethoxyphenyl; 2-bromo-6-chloro-4-trifluoromethylphenyl; 2-bromo-6b-chloro-4-trifluoromethoxyphenyl; 2,6-difluoro-4-rifluoromethylphenyl; 2-chloro-4-fluoromethylphenyl; 2, b-dichloro-3-methyl-4-trifluoromethylphenyl;

C-chloro-5-trifluoromethyl-2-pyridinyl; C-chloro-5-trifluoromethoxy-2-pyridinyl; C,5-dichloro-2-pyridinyl; 2,6-dichloro-4-bromophenyl; 2,4,6-trichlorophenyl; 2-bromo-6-fluoro-4-difluoromethylphenyl; 2-chloro-6-fluoro-4-trifluoromethylphenyl; 2,6-dibromo-4-trifluoromethylphenyl; 2,6-dibromo-4-trifluoromethoxyphenyl; and 2-bromo-4-trifluoromethylphenyl.

Next, the preferred substituents of 7 in formula (1) are the groups: acetylamino; amino; 2-n-butoxypropionylamino; /0 methyl; hydroxyacetylamino, ethyl; C-ethylsulfinylpropylamino; bromine; formylamino; chlorine; methylamino; ethylamino; 2-hydroxyethylamino; 2-methoxyethylamino; methylsulfonylamino 2-ethylsulfonylethylamino; 4-methoxybenzoylamino; 2-cyanoethylamino; 2-methylthioethylamino; 2-aminocarbonylethylamino (2-carbamoylethylamino); 2-methylsulfinylethylamino; C-methoxycarbonylpropylamino; 2-ethylsulfinylethylamino; 2-methylsulfonylethylamino; cyanomethylamino; 2-ethylthioethylamino; aminocarbonylmethylamino (carbamoylmethylamino); dimethylamino; 2-nitroethylamino; 2-acetylethylamino; methylcarbonylmethylamino (acetylmethylamino); methoxycarbonyl and ethoxycarbonyl.

Next, the preferred substituents of -5(0)0K5 in formula (1) are the groups: methylthio; methylsulfinyl; methylsulfonyl; ethylsulfinyl; ethylsulfonyl; ethylthio; cyclopropylsulfinyl; cyclopropylthio; cyclopropylsulfonyl; isopropylsulfinyl; isopropylsulfonyl and isopropylthio.

Particularly preferred pyrazole derivatives include the following (with numbers 1-11 assigned to these compounds for reference and identification purposes). 1. 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole-3-thiocarboxamide. 2. 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole-3-thiocarboxamide. 3. 4-dichlorofluoromethylsulfonyl-1-(2,4,6-trichlorophenyl)pyrazole-3-thiocarboxamide. ch 4. 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide. 5. 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfonylpyrazole-3-thiocarboxamide. i) 6. 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole-3-thiocarb-oxamide. 7. 5-amino-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide. 8. 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole-3-thiocarboxamide. 9. 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide. 10. 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole-3-thiocarb-oxamide. o 11. 5-amino-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-ethylsulfinylpyrazole-3-thiocarboxamide. M

Methods or processes of synthesis

Compounds of the general formula (I) can be obtained by applying or adapting known methods (i.e. methods that have been used or described in the chemical literature so far, including

Spetis!. Abrvigas) in which 3-cyano-1-phenylpyrazoles or intermediate compounds of the type

C-cyano-pyridinyl)pyrazoles of the known formula, or they can be obtained using methods or processes similar to those described in publications ЕРО295117, ЕРО234119, МУО87/03781, ЕРОБ500209 and

EP780378. "

According to the distinguishing feature of this invention, compounds of formula (I) can be obtained by reacting -ptv) with compounds of formula (II)

F in; Hm and A -I Z 2) 20 where Ki, Ko, Kz, Ki, Kv, M and 7 are defined as above, with alkali or alkaline earth metal hydrosulfide, such as lithium, potassium, calcium or preferably sodium hydrosulfide, in an inert solvent, for example, M,M-dimethylformamide, pyridine, dioxane, tetrahydrofuran, sulfolane, dimethyl sulfoxide, methanol or ethanol at a temperature from -35"C to 50"C, preferably from 0"C to 30"C. The hydrosulfide may optionally be formed by treatment with hydrogen sulphide (H 25 ) in the presence of an organic alkali such as 25o metal alcoholate or trialkylamine, or an inorganic alkali such as hydroxide or carbonate of an alkali or

F! alkaline earth metal such as sodium, potassium or ammonium carbonate. The use of a metal complexing agent such as a crown ether may be beneficial in accelerating the reaction. The reaction of the de hydrosulfide salt with 3-cyanopyrazole can also be carried out in a biphasic water/organic solvent system using an interfacial catalyst such as a crown ether or a tetraalkylammonium salt such as 60 for example tetra-n-butylammonium bromide or benzyltrimethylammonium chloride. Organic solvents suitable for use in a two-phase system with water include benzene, toluene, dichloromethane, 1-chlorobutane, and methyl tert-butyl ether.

Compounds of formula (1) can be obtained from compounds of formula (I) by treatment with the PP reagent, as described in the work of Thea. I ey., 24 (20), 2059 (1983). because In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where K., K»o, Kz,

Ku, Kv, M and 7 are defined as above, and in which n is 1 or 2, can be obtained by oxidation of the corresponding compounds of formula (1) in which H is 0 or 1. The reaction must be carried out with the help of a mild oxidizing agent (to prevent destruction of the thioamide functional group), such as sodium periodate, in an inert agent, such as dichloromethane, at a temperature from -407"C to the boiling point of the solvent.

According to the following distinguishing feature of this invention, compounds of the general formula (1), where 7 represents hydrogen, halogen, alkyl, haloalkyl, amino, KeMH- or KUKaiM-, where Kb, K7 and/or Ka represent alkyl, alkoxycarbonyl, formyl and -Z(O)ralkyl; or Ke and K; connected in such a way that together they form a divalent radical having from 4 to b carbon atoms in the chain, can be obtained using the 70 methods described in one or more publications of international patents MoMouuO94/21606, UUO93/06089 and

МО87/03781, in the publication of the European patent Мо0295117 and in the European patent ЕРБ511845, the US patent

Мо5232940 (authors of National Research Council of Ukraine) and German patent publications МООЕ19511269.

According to the following distinguishing feature of the invention, compounds of formula (1), where K., K", Kz, Ku, Kv and M are defined as above, and 7 represents K 6MH-, where Ke means ethyl substituted in position 2 by the Ko radical , where Co /5 represents Cyano, nitro, -5(O) 4Kio, -C(O)alkyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl, can be obtained by reacting the corresponding compound of formula (1), where 7 is an amino group, with a compound of the formula (PP):

Co-SNeCH»5 (PI) where Co is defined as above. The reaction may preferably be carried out in the presence of a base such as sodium hydride, an alkali metal hydroxide such as potassium hydroxide, or a tetraalkylammonium hydroxide such as M,-benzyltrimethylammonium hydroxide, in a solvent such as M,M-dimethylformamide, tetrahydrofuran, toluene, ethanol or water, and at a temperature from -207C to the boiling point.

In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where where K 4, K»o,

Kz, Ka, Kb" and M are defined as indicated above, and 7 represents -MNEK 5 or -MK7Ka, where K; and Ka represent lower alkyl or haloalkyl, optionally substituted by one or more Ko radicals, can be obtained by reacting the corresponding compound of formula (1), where 7 is an amino group, with the compound of formula (IM): i) 4-X ( M) where K.i4 is an alkyl or haloalkyl, optionally substituted by one or more K o radicals, and U is a leaving group, preferably a halogen (for example, chlorine). The reaction can be carried out in the presence of a base such as potassium hydroxide, potassium methylate, sodium hydride or triethylamine, in an inert solvent such as M,M-dimethylformamide, tetrahydrofuran, toluene or ether, and at a temperature of -207C to o boiling point. uh-

In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where 7 is an alkoxycarbonyl, can be obtained by reacting the corresponding compound of the formula (1), where 7 is a carboxyl group, with an alcohol of the formula (M): "o

K.29H (M) where Ki" is alkyl. The above-mentioned reaction is preferably carried out in the presence of an acid catalyst, such as sulfuric acid, generally in the presence of an excess of alcohol or, optionally, in a co-solvent, at a temperature from 0O7"C to the boiling point. Alternatively, the reaction can be carried out using of a coupling reagent, such as dicyclohexylcarbodiimide, in an inert solvent.

In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where 7 represents;" is an alkylthiocarbonyl, can be obtained by reacting the corresponding compound of the formula (1), where 7 is a carboxyl group, with an alcohol of the formula (MI):

KoZN (MI) b de Ki" represents an alkyl. The reaction can be carried out using a coupling reagent such as dicyclohexylcarbodiimide in an inert solvent.

Ш- In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where 7 represents -I is Ki3zCH(CI)CH»-, where Kis is alkyl, can be obtained by diazotization of the corresponding compound 5o of formula (1), in in which 7 is an amino group, with the following reaction with a compound of formula (MI): о ВИССНеСН (MI) и» The reaction is usually carried out using an alkyl nitrite, for example, tert-butyl nitrite, in the presence of a copper salt, such as copper (II) chloride, in solvent, such as acetonitrile, at a temperature from -107C to 5070.

In accordance with the following distinguishing feature of the invention, the compounds of the general formula (1), where 7 represents the -C(O)alkyl group, can be obtained by oxidizing the corresponding compound of the formula (MIP): 5 about BO. Iii ki, ko he vi-snki bo v; Sam

YOU TV

KE, 65 SL) where Ku, Ko, Kz, Ka, Kv, and M are defined as above, and K.4 represents alkyl. The reaction can be carried out,

for example, using a mixture of chromic acid and sulfuric acid in a solvent such as water and acetone at a temperature of 0°C to 60°C. The compounds of the formula (MI) are new and thus constitute the following distinguishing feature of the present invention. In accordance with the next distinguishing feature of the invention is that compounds of formula (1), where 7 is K./3CH-CH-, can be obtained by dehydrochlorination of the corresponding compound of formula (1), where 7 is K 13CH(CI)CH"-. The reaction is usually is carried out using an alkali, such as sodium hydroxide or triethylamine, in an inert solvent, for example, dichloromethane or tetrahydrofuran, at a temperature from -707C to the boiling point.

In accordance with the following distinguishing feature of the invention, compounds of the general formula (1), where 7 represents 70 is hydrazino, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl, can be obtained according to the methods described in the European patent ЕРОЗ52944 .

Intermediate compounds of the general formula (1), where 7 is a carboxy group, can be obtained by oxidizing the corresponding compound of formula (1), in which 7 is formyl. The reaction is usually carried out using potassium permanganate or chromic acid in a solvent such as water at a temperature from 0"C 7/5 to the boiling point.

Intermediate compounds of the formula (MI!) can be obtained by reacting the corresponding compounds of the formula (1), in which 7 is a formyl group, with an organometallic reagent of the formula K 450), where O is preferably an alkali or alkaline earth metal, for example, lithium or magnesium halide reagent (Grignard reagent).

The reaction can be carried out in an inert solvent, such as ether or tetrahydrofuran, and at a temperature from 778°C to the boiling point of the solvent.

Intermediate compounds of formula (1), in which 7 is a formyl group, can be obtained by oxidation of the corresponding compound of formula (1), in which 7 is a Kiz3CH-CH- group. The reaction is usually carried out using such a reagent as ozone or sodium metaperiodate, in an inert solvent, for example, dichloromethane, at a temperature from -1007C to 100"C. Some compounds of formula (II) are new and in this capacity form the following distinguishing feature of this invention.

Intermediate compounds of formulas (I) and (IM) are known or can be obtained using known methods. and)

Exemplary specific compounds of formula (1) according to the present invention are presented in Table 1 below. In the table, c-Pg means cyclopropyl, CHNHCH means a propargyl group, and i-C3H7 means isopropyl. « zo so i-

GT

Fo 6 vosna mne vbnods nos « 0 80 ovoson mne nos nos 2 s 8 vosni mne non osv nos

And what's more

F

IN

- c) their schi o o i b5 31 8Oosna MNSnNosSnNoOSNnI SINO (SEz |sNZ|ССИ o

I

The invention is illustrated by the following examples, which are not to be construed as limiting the invention, but are given to better demonstrate its application.

Example 1 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole-3-thiocarboxamide

To a stirred solution, 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-methylthiopyrazole (4.7 g) and 5 drops of 15-crown-5 in degassed M,M- to dimethylformamide, a solution of sodium hydrosulfide hydrate 17 (0.79 g) in degassed water was added over several minutes. The mixture was stirred at 207C for 18 hours, 29 was evaporated and the residue was purified by flash chromatography on silica gel, eluting with He) with a mixture of hexane/acetone 21 to obtain 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl) -4-methylthiopyrazole-3-thiocarboxamide (0.38 g), T. pl. 1617C (compound 1).

Using a method similar to the method used above, compounds with numbers 2 to 11 of the general formula (1), shown in Table 2 below, were also synthesized. s v - » Ф 8 veni nosivosno Mo tv, ch o - - vv nobta noosivosan Mne vt chi v nonbta noosivosno mno vav, ia Reference example 1 -I 5-amino-1-(2,4,6-trichlorophenyl)-3 -cyanopyrazole

Sodium nitrite (27.bg) was slowly added to concentrated sulfuric acid (1Oml) and the mixture was poured

It was cooled to 30°C. Acetic acid (216 bml) was added to the stirred mixture over 30 minutes, which

Ge) 20 was cooled to 20°C and a solution of 2,4,6-trichloroaniline (70.7g) in acetic acid was added over 30 minutes, maintaining the temperature at 20-257°C. The mixture was heated to 52"C for 30 minutes, then it was served

T" for 20 minutes, a solution of ethyl 2,3-dicyanopropionate (52.0 g) in a 3695 aqueous solution of acetic acid (774 ml), while cooling to 10-157C. The reaction mixture was allowed to warm to 20"C, diluted with water and extracted with dichloromethane. Then the organic layer was washed with a dilute ammonium hydroxide solution and mixed with 2990 29 ammonium hydroxide solution for 17 hours. The organic phase was washed with water, then with hydrochloric acid (1H), (FI was dried (Mo5O ,) and evaporated. Crystallization from toluene gave t B-amino-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (32.82 g), "NMR (SOCI5): MH" (2H, w.s, 3.v4 million), 4-H (1H, c, 5.97 million"), arom. (2H, c, 7.5C million"). in Reference example 2 5-amino-4-dichlorofluoromethylthio-1-(2,4 , b-trichlorophenyl)-3-cyanopyrazole

To a stirred solution of 5-amino-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (8.0 g, 0.028 mol) in acetic acid (U/U0 mL) was added dichlorofluoromethylsulfonyl chloride (4.4 mL) over 5 minutes The mixtures were allowed to stir at 20 C for 65 hours, then poured into water and extracted with dichloromethane. c5 The organic phase was washed with a cold solution of sodium bicarbonate, then with water, dried (MosO)) and evaporated. Column chromatography on silica gel eluting with a mixture of dichloromethane/hexane 3:1 gave

5-amino-4-dichlorofluoromethylthio-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (6.06bg), T. pl. 189-19176.

Reference example C 4-Dichlorofluoromethylthio-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole

A solution of 5-amino-4-dichlorofluoromethylthio-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (2.19 g) and tert-butyl nitrite (9090, 4.1 mmol) in tetrahydrofuran was heated under reflux for 3, 5 hours and evaporated.

The residue was purified by flash chromatography on silica gel, eluting with dichloromethane to obtain 4-dichlorofluoromethylthio-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (1.56 g), T. pl. 106-10870.

Reference example 4 70 4-Dichlorofluoromethylsulfonyl-3-cyano-1-(2,4,6-trichlorophenyl)pyrazole

A solution of 4-dichlorofluoromethylthio-3-cyano-1-(2,4,6-trichlorophenyl)pyrazole (0.80 g) and 3-chloroperbenzoic acid (8095, 0.86 g) in chloroform was heated under reflux for 2 hours, cooled, diluted with ethyl acetate and successively washed with 1095 sodium hydrosulfite, 2N. Mason, water and saturated saline solution. The dried (M9504) solution was evaporated and purified using flash chromatography on silica gel, eluting with dichloromethane Kk! obtaining 4-dichlorofluoromethylsulfonyl-1-(2,4,6-trichlorophenyl)-3-cyanopyrazole (0.41g), T. pl. 143.5-14576.

Reference example 5 5-Amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole

Stage 1

Bromine (0.5ml) was added over 10 minutes to a stirred solution of sodium thiocyanate (1.7g) in anhydrous methanol at -6576. A solution of 5-Amino-1-(2-chloro-4-trifluoromethylphenyl)-33-cyanopyrazole (1.5 g) in anhydrous methanol was added over 10 minutes, and the stirred mixture was allowed to warm to 207C for 16 hours. After pouring into water, the precipitate was collected and dried to obtain 5-amino-1-(2-chloro-4-fluoromethylphenyl)-3-cyano-4-thiocyanatepyrazole (1.64 g). HPLC (C-18 column, eluting with a mixture of CH2STt/H2O 31 at 1.Oml/minute) showed the compound as a peak with an area of 86.695 at an elution time of 5.11 minutes. (8)

Stage 2

Iodomethane (0.7 mL) was injected into a suspension of 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyano-4-thiocyanate-pyrazole (1.64 g) in stirring methanol at 1095 aqueous sodium hydroxide solution (2.8 ml) was added and the reaction mixture was stirred continuously. 1 hour at 4"C, poured into water and extracted with dichloromethane and ethyl acetate. The dried (Ma»5Od) combined with the organic phase was evaporated and purified using flash chromatography on silica gel, eluting with a mixture of hexane/ethyl acetate 4:1 with obtaining, after trituration with a mixture of hexane/dichloromethane, 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyano-4-methylthiopyrazole (0.4 g), T. pl. 129-13276. i-

Stage C "o

3095 hydrogen peroxide (0.5 ml ) upon cooling to 47C. The temperature of the mixture was brought to 20"C for 2 hours, then it was poured onto ice and the solid phase was washed with water and dried.

Flash column chromatography on silica gel gave "5-amino-1-(2-chloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole (0.69 g), T. pl. 146-1477S. with c Reference example 6. Using a method similar to that used in Reference Example 5, stages 1 and 2, there were also the following compounds were obtained: 5-amino-1-(2,6-dichloro-4-trifluoromethoxylphenyl)-3-cyano-4-methylthiopyrazole, T. pl. 147-1487C, and 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-3-cyano-4-methylthiopyrazole, T. pl. 178-180".

Ge" Reference example 7

Using a method similar to that used in Reference Example 5, stage 3, were also obtained

Ш- the following compounds: 5-amino-1-(2,6-dichloro-4-trifluoromethoxylphenyl)-3-cyano-4-methylsulfinylpyrazole, T. pl. -I 137-138"С, and 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole, T. pl. 150-15176.

Biological effectiveness o In order to apply the compounds according to the present invention and to observe the results obtained in this case, the following methods were used: active on the leaf / contact aerosol (spraying solution) against suckers (aphids) or chewers (scale insects) insects The tests were carried out on the following types: and about the essay MY vol

Test with soil impregnation (systemic effect) because cotton and sorghum seedlings were rooted in pots. One day before processing, each pot was infected with aphids from a mixed population in the amount of about 25 individuals. Cotton sprouts were infected with cotton aphids, and sorghum sprouts were infected with grain aphids. The selected compounds of formula (1) were applied to the soil surface in such a dilution that gave the equivalent of a concentration in the soil of 100 parts per million by mass. on untreated control plants.

Contact bait test for houseflies (Myssa dotevziisa)

About 25 adult houseflies aged four to six days were anesthetized and placed in a pond with a sugar solution as bait in water containing the compounds. The concentration of the selected compound of formula (1) in the bait solution was 100 ppm! After 24 hours, flies that did not move when stimulated were considered dead.

Test of contact action on a leaf relative to the species A. Sovzvzuria

Cotton seedlings infected with aphids were placed on a rotating rotary wheel and sprayed to an excess of the drug with a composition containing 100 parts per million of the compound of formula (1). dead individuals of the background. 70 Compounds 1-11 according to the present invention showed activity against A. dozzuria and ZsPpiherpiv dgatipit at a concentration of 10 ppm7 in the above-mentioned systemic action test; against Myssa dotewiis at a concentration of 100 ppm." in the above-mentioned contact action lure test; and against Arpi dozzuriya at a concentration of 100 parts per million 7 in the above-mentioned test of contact action on a leaf.

The present invention proposes a method of systematic control of arthropods in the areas of damage, 79 especially with some insects or mites that feed on plant parts located above the ground.

Control of such leaf-damaging pests can be carried out by direct application to the leaves or application, for example, by spraying on the soil or applying granules to the roots or seeds of plants, followed by systemic transfer to above-ground plant parts. Such systemic activity includes the fight against insects that are not only at the place of application, but also on removed parts of the plant, for example, due to transfer from one side of the leaf to the other or from a treated leaf to an untreated leaf. Examples of classes of insect pests that can be systemically controlled with the compounds of this invention include Notoriega (stinging-sucking), Netiriega, and Tpuzaporiega. This invention is particularly suitable for combating aphids and thrips.

As follows from the previous pesticidal use, the present invention proposes pesticidally active compounds and methods of using these compounds to combat a number of insect species, which includes: o arthropods, especially insects or ticks; plant nematodes; or helminths or protozoan pests. The compounds of formula (1) or their pesticidally acceptable salts are advantageously used for practical purposes, for example, in agriculture or horticulture, in forestry, veterinary medicine or animal husbandry, or for health protection purposes. Here and in those cases where the term "compounds of formula (1)" is used, this term includes - compounds of formula (1) and their pesticidally acceptable salts. The term "compounds of formula (1)" includes compounds of formula (1) c and its pesticidally acceptable salt.

Therefore, the present invention provides a method of controlling pests at the site of the lesion, which includes treating the site (for example, by applying or injecting) an effective amount of a compound of formula (1) or a pesticidally acceptable salt thereof, where the substituent groups are defined above. The place of application includes, for example, the pests themselves or 3o Place (plant, animal, field, building, house with an adjacent plot, forest, greenhouse, reservoir, soil, ise) plant or animal product or the like) where these pests are or eat.

The compounds of this invention can, in addition, be used to control soil insects such as long-bearded fleas, termites (especially for the protection of structures), root grubs, wireworms, root weevils, "grinders, scoops, root aphids or grubs." they can also be used to provide activity against plant pathogenic nematodes such as gall, cyst, (dagger, in damaged areas), stem or c) bulb nematodes, or against mites. To combat soil pests, for example, with the long-bearded flea, the compounds are conveniently applied or applied in an effective amount to the soil in which the plants are planted or will be planted, or to the seeds or roots of growing plants.

In the field of public health, these compounds are particularly useful in the control of many insects, especially dung flies or other Diptera pests such as houseflies, autumn fireflies, lionflies,

Cow weevil, deer thrips, horse hornet, small dipterous insects, woodlice, carrion fly or mosquitoes. -I Compounds of this invention can be used in the following applications and to control the following pests, including arthropods, especially insects and mites, nematodes or helminths, or the simplest - pests. oo 50 For the protection of stored products, for example, cereals, including grain or flour, peanuts, livestock products, timber or household treasure, for example, carpets and textiles, the compounds of the present invention can be used against attack by arthropods, especially beetles, including weevils, moths and mites, for example, ErPpeuzia srr. (flour moth), Apigepis spp. (antrenus), Tgiroiyshz zvrr. (Khrushchik flour), 5iorpiiz zrr. (grain weevil) or Asagiz sr. (pincers).

For the control of cockroaches, ants or termites or similar arthropod pests in

F! infested residential or industrial premises, or to control mosquito larvae in reservoirs, wells, tanks or other types of standing or flowing water. where To treat foundations, structures or soil to prevent termite attack on structures, e.g.

Keiiispiiegtez vrr., Ne(egoiegtez vrr., Sorioiegtez srr. 6o In agriculture against adults, larvae and eggs of Ieridoriega (butterflies and moths), for example, Neioipiz vrr., such as Neioipiz migezsepz (scoop), Neioipov aptidega and Neioiiiz gea. Against adults or larvae of Soieoriega (beetles), e.g. Apipopotis spp., e.g.

Neijegorieega (Neptiriega apa Notoriega), for example, Rzuia sr., Vetivia sr., Tgiasheigodez 5Zr., Arpiv sr., bo Mudgpz sr., Medoiga missiae, RpuiPohega sr., Merpoiientisich sr. (hise Ia? grasshoppers), Miiaragmaya sr.

Against Oirieg, for example, Mizza vzrr., against Tpuzaporieg, such as TNhirz garasi. Against Ohiporiega, such as Gosivia apa Zspiviosegsa spp., (locusts and crickets), e.g. OguP5 spp., and Aspeia spp., e.g.

Viatsa ogiepra|iyz, Regiriapebya ategisapa, Viafeya degptapisa, Iospvia tidgayogia tidgayugioidev ("

Zspiviosegsa dgedagia. Against SoPettroia, for example, Regiriapeia co. and Viaceia srr (cockroaches).

Against arthropods of agricultural importance, such as Asagi (mites), for example, Te(hapuspiz gr., and Rapopuspiz vrr.

Against nematodes that damage plants and trees and present a danger to agriculture, forestry or horticulture either directly or by spreading bacterial, viral, mycoplasma or 7/0 fungicidal plant diseases. For example, nodule nematodes such as Meioidodupe spp. (for example, M. ipsodpi(a).

In the field of veterinary or animal husbandry or public health against arthropods, helminths or protozoa parasitic within or on the bodies of vertebrates, especially warm-blooded vertebrates, e.g. domestic animals, e.g. cattle, sheep, goats, horses, pigs, birds , dogs or cats, e.g. Asagipa, including ticks (e.g.

Ogpiyodogiz toibraiia) and ticks (for example, Oataiimpia vrr.); Oiriega (for example, Aedez srr., Aporpeiz 2rr.,

Myvzsa ovzrr. Nurodepta Ltd.); Netiriega; Oisiuoriega (for example, Regiriapeba spp., ViayeMya spp.);

Nuteporiega; for example, against infections of the gastrointestinal tract caused by parasitic nematode worms, for example, members of the family Tgispovigopduiidae; for the control and treatment of protozoal diseases caused by, for example, Eitegia spp., for example, Tgurapozotv sgp?i,

And eivpatipia zrr., Riaztodaitst zgrr., Vabezviz zrr., Tgispotopadiadeee vrr., Tokhoriazta zrr. and Tneiiegia Co., Ltd.

In practical use for the control of arthropods, especially insects or mites, or nematodes - pests of plants, the method, for example, includes applying to the plants or to the environment where they grow, an effective amount of the compound of this invention. In this method, the active compound is usually applied to the site where it is necessary to control the infestation by arthropods or nematodes, in an effective i) amount in the range of about bg to about ikg of the active compound per hectare of the treated area. Under ideal conditions, depending on the pest to be destroyed, lower doses may provide adequate protection. On the other hand, adverse weather conditions, persistence of pests or other factors may require higher doses of the active ingredient. The optimal amount usually depends on a number of factors, for example, on the type of pest to be destroyed, on the type or stage of development of infected plants, the distance and between rows, as well as on the method of application. More preferably, the effective amount of the active compound should be in the M range from about 50g/ha to about 40O0g/ha.

If the pest is released into the ground, the active compound (usually in the composition) is distributed evenly over the surface to be treated (ie, for example, sprayed over the entire surface or treated in strips) by any convenient method, and applied in doses from about 5g to about kg AI/ha (AI-active ingredient), preferably from about 50 to about 250g AI/ha. When applied in the form of soaking the roots of seedlings or by drip irrigation of plants, the liquid solution or suspension contains from about 0.075 to about 100 Ωg ai/l, preferably from about to about 200 mg ai/l. Application can be carried out, if desired, on the entire surface of the field or site, where "

Grow any culture, or in close proximity to seeds or plants that need protection. in c The active component can be washed into the soil by spraying the entire surface with water, or it can be left until the natural action of rain. During or after application of the compound in the composition, it is possible, if desired, to distribute mechanically in the soil, ;" for example, when plowing, when discing, or using a chain train. Application can be made before planting, during planting, after planting, but before the appearance of sprouts, or after the appearance of sprouts.

The compounds of this invention and the pest control methods proposed herein represent a special

Ge" value in the case of protection of fields, fodder plants, plantations, greenhouses, greenhouses or vineyards, ornamental plants, planting trees or trees in the forest, for example: cereals (such as wheat or rice), cotton, vegetable plants (such as pepper ), field crops (such as sugar beets, soybeans or oilseed rape), grasslands or forage crops (such as corn or sorghum), orchards and groves (such as stone or seed or citrus), ornamentals, flowers or vegetables or shrubs under glass or in gardens and parks, or forest trees (both deciduous and evergreen) in the forest, in plantings or in nurseries. They are also of value in protecting timber (standing, fallen, processed, stored or in structures) from attack by, for example, sawflies, beetles or termites.

They are used to protect stored products such as grain, fruit, nuts, spices or tobacco, either whole or ground or processed into products, against attack by moths, beetles, mites or barnacle weevils. Animal products such as skin, hair, wool are also protected

F) or feathers in natural or processed form (for example, in the form of carpets and textiles) from the attack of moths or beetles, as well as stored meat, fish or grain from the attack of beetles, mites or flies.

In addition, the compounds of the present invention and methods of use thereof are of particular value for the control of arthropods, helminths or protozoa which infect, or spread, or carry diseases of domestic animals, such as those already mentioned, and more specifically, for control of ticks, ticks, lice, fleas, small dipterous insects or biting, annoying or thujavziz flies.

The compounds of this invention are particularly useful for controlling arthropods, helminths or protozoa that inhabit pet hosts, or that feed within the body or on the skin, or that suck 65 the blood of animals, and for this purpose they can be administered orally, parenterally, transdermally or superficially.

In addition, the compounds of this invention may be useful in the fight against coccidiosis, a disease caused by infection with protozoan parasites of the genus Eitegia. It is an important potential cause of economic losses in the breeding of domestic animals and poultry, especially those that are grown or kept under intensive conditions. For example, cattle, sheep, pigs or rabbits can be affected, but the disease is especially dangerous for poultry, especially chickens. Administration of a small amount of the compound of this invention, preferably in combination with feed, effectively prevents or significantly reduces the possibility of coccidiosis. These compounds are effective against both cecal and intestinal forms. In addition, the compounds of this invention can also have an inhibitory effect on oocytes, significantly reducing their number and sporulation. Poultry diseases are usually spread by birds ingesting infectious 70 organisms in droppings, litter, on litter, on the ground, in feed or drinking water. The disease is manifested by bleeding, accumulation of blood in the appendix, the appearance of blood in excrement, weakness and indigestion.

The disease often ends in the death of the animal, but a bird that survives a serious infection loses significantly in market value as a result of the infection.

The compositions, which are further described for applying to growing crops or applying to areas where 7/5 agricultural crops are grown, or for coating seeds, can generally be used in another version for surface application to animals or for the protection of stored products, domestic utensils, estates or environmental districts. Suitable means of applying the compounds of this invention include: - for growing crops - aerosols, duets, granules, mists or foams intended for foliar treatment, or in the form of a suspension of finely ground or encapsulated compositions in the form of soil or root treatment with liquid irrigation, duets, granules, smoke or foams; on plant seeds by coating the seeds with liquid suspensions or duets; - on animals infected: or prone to infection with arthropods, helminths or protozoa, by parenteral, oral administration or surface application of a composition in which the active ingredient exhibits immediate and/or prolonged action over a period of time against arthropods, helminths or protozoa, e.g. by inclusion in feed or in appropriate pharmaceutical compositions absorbed by oral administration, in edible baits, salt brines, food additives, bulk compositions, and) sprays, baths, showers, washing, spraying, duets, ointments, shampoos, creams, waxy ointments or body self-treatment systems; - for the environment in general or for specific places where pests can hide, "E zo Including stored products, lumber, household supplies or residential or industrial premises, in the form of sprays, fogs, duets, fumigations, waxy ointments, varnishes, granules or baits, or in the form of droppers for reservoirs, wells, reservoirs or other flowing or stagnant water; M - for domestic animals in feed to combat fly larvae that feed in their feces.

In practice, the compounds of this invention most often constitute parts of the composition. These compositions can be used to fight against: arthropods, especially insects or ticks; nematodes; or helminths or the simplest pests. The compositions may be of any type known to those skilled in the art for use against the desired pest in any indoor or outdoor environment, or by internal or external administration to vertebrates. These compositions contain at least one compound of formula (1) or a pesticidally acceptable salt thereof, as previously described, as an active ingredient in combination or combination with one or more of the other compatible components, which are, for example, solid or liquid carriers or diluents, adjuvants, with surface-active agents or the like, suitable for the intended use, and which are acceptable for . application in agriculture and medicine. These compositions, which can be obtained by any method known to those skilled in the art, also form part of the present invention.

These compositions may also contain other types of ingredients such as protective colloids, adhesives, thickeners, thixotropic agents, permeability enhancing agents, spray oils (especially for acaricidal

Ge" application), stabilizers, preservatives (especially anti-mould preservatives), sequestering agents or the like, as well as other known ingredients having pesticidal properties (in particular, insecticidal, schmiticidal, nematicidal or fungicidal) or having properties regulation of plant growth -I. In a more general formulation, the compounds used in the present invention may be combined with any solid or liquid additives suitable for conventional formulation methods. and Compositions suitable for use in agriculture, horticulture, etc., include compositions suitable for use as, for example, sprays, duos, granules, mists, foams, emulsions, or the like.

Doses of compounds that are effectively used in the present invention can vary widely, particularly depending on the nature of the pest to be destroyed, or on the degree of contamination, for example, of agricultural crops, by these pests. Typically, the compositions of the present invention contain from about 0.05 to about 9595 (by weight) of one or more of the active ingredients of the present invention, from about 1 to about

F) 9595 of one or more of solid or liquid carriers and, optionally, from about 0.1 to about 5095 of one or more of other compatible components, such as surface-active agents or the like.

In the text under consideration, the term "carrier" means an organic or inorganic ingredient, natural or synthetic, with which the active ingredient is combined to facilitate its application, for example, to plants, seeds or soil. Therefore, such a carrier is usually inert, and it must be acceptable (for example, agronomically acceptable, especially for plant processing).

Carriers can be solid, for example, clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (eg, ammonium salts), ground natural 65 Minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite , bentonite or diatomaceous earth, or crushed synthetic minerals such as silicon dioxide, aluminum oxide or silicates, especially aluminum or magnesium silicates. Suitable solid carriers for granules are: crushed or fractionated rocks, such as calcite, marble, pumice, sepiolite and dolomite; synthetic pellets of inorganic or organic flour, pellets of organic materials such as sawdust, coconut husks, corn cobs, corn husks or tobacco stalks; diatomaceous earth, tricalcium phosphate, powdered bark or absorbent carbon black; water-soluble polymers, resins, wax; or solid fertilizers. Such solid compositions may optionally contain one or more compatible wetting, dispersing, emulsifying or coloring agents which, if solid, may also serve as diluents.

Carriers can also be liquid, for example, water, alcohols, especially butanol or glycol, as well as their 7/0 simple or complex ether, especially methyl glycol acetate; ketone, especially acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone or isophorone; petroleum fractions, such as paraffinic or aromatic hydrocarbons, especially xylenes or alkylnaphthalenes; mineral or vegetable oils; aliphatic chlorinated hydrocarbons, especially trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, especially chlorobenzenes; water-soluble or strongly polar solvents such as dimethylformamide, dimethylsulfoxide or M-methylpyrrolidone; liquefied gases; or the like, or their mixtures.

The surface-active agent can be an emulsifying agent, a dispersing agent or a wetting agent of the ionic or non-ionic type, or a mixture of such surface-active agents. Among them are possible, for example, salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenylsulfonic or 2o-naphthalenesulfonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids, or fatty esters or fatty amines, substituted by phenols (especially alkylphenols or arylphenols), salts of esters sulfosuccinic acid, taurine derivatives (in particular, alkyltaurates), complex phosphoric ester of alcohols or polycondensates of ethylene oxide with phenols, complex ester of fatty acids with polyols, or sulfate, sulfonate, or phosphate functional derivatives of the aforementioned compounds. high school

The presence of at least one surface-active agent is usually essential if the active ingredient and/or the inert carrier are only slightly soluble in water, or insoluble in water, and the carrier of this composition for application is water. and)

The compounds of this invention may further contain other additives, such as adhesives and dyes. Adhesives such as carboxymethyl cellulose, or natural or synthetic polymers in the form of powders, granules or gratings, such as gum arabic, polyvinyl alcohol or polyvinyl acetate, natural phospholipids such as cephalins or lecithins, or synthetic phospholipids can be used in these compositions. Dyes such as inorganic pigments such as iron oxides, titanium oxides or Prussian blue can be used; organic dyes, and such as alizarin dye, azo dye or metal phthalocyanine dyes; or micronutrients such as M salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.

Compositions containing compounds of formula (1) or their pesticidally acceptable salts, which can be used to control arthropods, plant nematodes, helminths or protozoan pests, may also contain synergists (for example, piperonyl butoxide or sesamex), stabilizers, other insecticides , acaricides, plant nematicides, agents for controlling helminths or coccidiosis, fungicides (for agricultural or veterinary use, e.g. benomyl and iprodione), bactericides, attractants or repellents or pheromones for arthropods or vertebrates, deodorants, flavoring agents, dyes or « auxiliary therapeutic agents, for example, trace elements. Such compositions can be created to increase efficiency, stability, safety, absorbability where it is needed, to expand the spectrum. pests that can be combated, or to give the composition the ability to perform other useful functions and? in relation to the same animals or areas to be processed.

Examples of other pesticidally active compounds that can be included in the composition or used together with

The compositions of this invention are: acephate, chlorpyrifos, demeton-5-methyl, disulfoton, ethoprophos,

Ge" fenitrothion, fenamiphos, phonophos, isazophos, isofenphos, malathion, monocrotophos, parathion, phorate, phosalon, pirimifos-methyl, terbuphos, triazophos, cyflugrin, cypermethrin, deltamethrin, fenpropathrin, fenvalerate,

Sh- permethrin, tefluthrin, aldicarb, carbosulfan, methomyl, oxamyl, pirimicarb, bendiocarb, teflubenzuron, -I dicofol, endosulfan, lindane, benzoximate, cartap, cihexatin, tetradifon, avermectins, ivermectins, milbemycins, thiophanate, trichlorfon, dichlorvos, diaveridine or Dimetriadazole. o For use in agriculture, the compounds of formula (1) or their pesticidally acceptable salts are usually in the form of various solid or liquid compositions.

Solid forms of compositions that can be used are duets (containing a compound of formula (1) or its pesticidally acceptable salt, in the range up to 8095), wettable powders or granules (including water-dispersible granules), in particular those obtained by extrusion, pressing, by impregnation of a granule carrier or by granulation, starting from a powder (the content of the compound of formula (1) or its pesticidally acceptable salt in such (F, wettable powders or granules is from about 0.5 to about 8095). Solid homogeneous or heterogeneous ka compositions containing one or more of the compounds of formula (1) or their pesticidally acceptable salts, e.g. granules, tablets, briquettes or capsules, can be used to treat flowing or stagnant water over a period of time A similar effect can be achieved using continuous or portioned water dispersible concentrates , as specified herein Liquid compositions include, for example, aqueous or non-aqueous solutions or suspensions (such as emulsifiable concentrates, emulsions liquid compositions, dispersions or solutions) or aerosols. Liquid compositions also include, but are not limited to, emulsifiable concentrates, dispersions, emulsions, flowable formulations, aerosols, wettable powders (or spray powders), dry powders, or pastes, such as 65 forms of compositions that are liquid or intended to form liquid compositions , for application, for example, in the form of water sprays (including small and ultra-small volumes) or in the form of mists or aerosols.

Liquid compositions, for example in the form of emulsifying or soluble concentrates, most often contain from about 5 to about 8Owag.95 of the active ingredient, although emulsions or ready-to-use solutions in their case contain from about 0.01 to about 2095 of the active ingredient . In addition to the solvent, emulsifiable or soluble concentrates

May contain, if necessary, from about 2 to about 5095 of suitable additives, such as stabilizers, surface-active agents, permeability-enhancing agents, corrosion inhibitors, dyes or adhesives. Emulsions of any desired concentration, which are particularly suitable for application, for example, to plants, can be obtained from these concentrates by diluting them with water. These compositions are included in the scope of compositions that can be used in the method of this invention. Emulsions can be water-in-oil or oil-in-water, and they can have a thick 7/0 consistency.

The liquid compositions of the present invention may, in addition to normal agricultural use, be used, for example, to treat substrates or areas infested or likely to be infested with arthropods (or other pests that can be controlled with the compounds of the present invention), including structures, outdoor or internal storage or process areas, containers or equipment, or 7/5 standing or running water.

All of these aqueous dispersions or emulsions or sprayable mixtures can be applied, for example, to cultivated plants, by any suitable method, mainly by spraying in doses which are usually from about 100 to about 1200 liters of the sprayable mixture per hectare, but may be higher or lower (for example, small or ultra-small volumes), depending on the need or the technique used. Compounds or compositions according to these inventions are conveniently applied to vegetative parts and, in particular, to roots or leaves; on which there are pests to be destroyed. Another method of application of the compositions or compounds according to this invention is application by chemicalization, simply put, by adding the composition containing the active ingredient to the water of irrigation facilities. Such irrigation can be done by spraying for foliar pesticides, or it can be surface irrigation for s ge Soil or for systemic pesticides.

Concentrated suspensions that can be applied by spraying are prepared in such a way as to obtain i) a suitable liquid product that does not settle (fine grinding) and usually contains from about 10 to about 75 wt.90 of active ingredient, from about 0.5 to about 3095 per surface active agent, from about 0.1 to about 1095 thixotropic agents, from about 0 to about 3095 of suitable additives such as antifoam agents, corrosion inhibitors, stabilizers, permeability improving agents, adhesives and, as a carrier, water or organic liquid, in which the active ingredient is sparingly soluble or insoluble. Some organic solids or inorganic salts can be dissolved in a carrier to prevent sedimentation or used as water antifreeze. M

Wettable powders (or spray powders) are usually prepared to contain from about 10 to about 8 parts of active ingredient, about 20 to about 9095 of solid carrier, about 0 to about 596 of wetting agent, about 3 to about 1095 of a dispersing agent and, optionally, about 0 to about 8095 of one or more stabilizers and/or other additives such as permeation agents, adhesives, anti-caking agents, dyes, or the like. To obtain such wettable powders, the active ingredient(s) are thoroughly mixed in a suitable mixer with additional substances, which can be impregnated with a porous filler, and ground using a mill or other suitable grinder. As a result, wettable powders are obtained, the wetting and suspendability of which is an important property. they can be suspended in water to obtain any desired concentration, and this suspension can be used with great success, in particular, for application to the leaves of plants. ;" "Water-dispersible granules (M/US)" (granules that are easily dispersed in water) have compositions that are practically close to the compositions of wettable powders. they can be obtained by granulation or preparation, as indicated for wettable powders, or by a wet process (by contacting finely divided active

He" of the ingredient with an inert filler or a small amount of water, for example, from 1 to 2Owag.9o, or with an aqueous solution of a dispersing agent or binder, followed by drying and sieving), or by a dry method

Sh- (pressing followed by grinding and sieving). -I Doses and concentrations of the obtained compositions may vary depending on the method of application or the nature of the composition or its use. Generally speaking, application compositions for the control of arthropods, plant nematodes, helminths, or protozoan pests usually contain from about 0.0000195 to about 9595, more preferably from about 0.000595 to about 5Owag.90 of one or more of the compounds of the formula (1) or their pesticidally acceptable salts, or all active ingredients (i.e. compounds of formula (1) or its pesticidally acceptable salts, together with: other substances toxic to arthropods or plant nematodes, agents against helminths and coccidiosis, synergists, trace elements or stabilizers ).

The compositions that are actually used and the doses of their introduction must be chosen to achieve the desired

F) the effect(s) on a farmer, animal breeder, doctor or veterinarian, pest control operator or other specialists.

Solid or liquid compositions for surface application to animals, lumber, stored products, or household utensils typically contain from about 0.0000595 to about 9095, especially from about 0.00195 to about 1095, by weight of one or more of the compounds of formula ( 1) or its pesticidally acceptable salts. For administration to animals either orally or parenterally, including transdermal administration, the solid or liquid compositions typically contain from about 0.195 to about 900 mg of one or more of the compounds of formula (1) or their pesticidally acceptable salts. Medicinal feed additives usually contain from about 0.00195 to about 95 wt. of one or more 65 of the compounds of formula (1) or pesticidally acceptable salts thereof. Concentrates or additives for mixing with feed usually contain from about 595 to about 9095, preferably from about 595 to about 5Owag.9o of one or more of the compounds of formula (1) or their pesticidally acceptable salts. Mineral salt brines usually contain from about 0.195 to about 1Owag.95 of one or more of the compounds of formula (1) or their pesticidally acceptable salts.

Duos or liquid compositions for application to livestock, goods, premises or outdoor areas may contain from about 0.000195 to about 1595, especially from about 0.00595 to about 295, of one or more of the compounds of formula (1) or their pesticidal acceptable salts. Corresponding concentrations in treated waters range from about O0.0001 parts. per million to about 20 parts. per million, especially from about 0.00 parts. per million up to about 5. per million, one or more of the compounds of formula (1) or their pesticidally acceptable salts, and may

And Iv 2

Example 2A

Prepare a water-soluble concentrate of the following composition: c 25 Active ingredient 7905 o

Eshuiap VSR 1095

T-methylpyrrolidone 8395

The active ingredient is added to the ESHUiap VSR solution, dissolved in a portion of M-methylpyrrolidone, while heating for 30 minutes and stirring until dissolved. The volume of the obtained solution is adjusted to the required solvent, which is left over.

Example 28 -

Emulsifiable concentrate (EC) of the following composition is prepared: - 325 Active ingredient 2595 (Max) o

Zorgorpog VZ 1095

Aguap SA B

M-methylpyrrolidone BO « o

Zoimev5o 150 1095 -in s The first three components are dissolved in M-methylpyrrolidone and then boimevzvo 150 is added to it to the final volume.

Example 20

A wettable powder of the following composition is prepared: (22) Active ingredient 4095 - I Aguap 5 290 bagap Mo2 B - Seiye RE 5Z9B o 50

All ingredients are mixed and ground in a hammer mill into a powder with a particle size of less than 5µm. iz" Example 20

Prepare an aqueous liquid composition of the following composition:

Active ingredient 40.0095

Eshuiap VSR 1.00965 o Zorgorpop T36 0.2095 ko Ethylene glycol Buv

Come on! 23 0.159 in Water 53.65

All ingredients are thoroughly mixed and ground in a ball mill to an average particle size of less than

Close

Example 2E 65 An emulsified suspension of the following composition is prepared:

Active ingredient 30,095

Eshuiap HRV 10,096

Vepiop 38 OB

Zoimevzvo 150 59, BU

All ingredients are thoroughly mixed and ground in a ball mill to an average particle size of less than

Close

Example 2E 70 Dispersing granules in water with the following composition are prepared:

Active ingredient 3095 bagap Mo2 1595

Aguap 5,890

Seiye RE ATO

All ingredients are mixed, finely ground in a liquid mill (Yashid-epegdu tii), and then granulated in a rotary granulator, spraying with water (up to 1095). The resulting granules are dried in a fluidized bed dryer to remove excess water.

Example 20

The powder for pollination of the following composition is prepared:

Active ingredient from 1 to 1095

Ultrafine talc powder from 99 to 9095 c

The ingredients are thoroughly mixed and then ground, if necessary, to a fine powder. This powder can be applied to an arthropod-infested area, such as a landfill, food storage, or household, or to animals infected or at risk of arthropod infestation for arthropod control by oral ingestion. Suitable means of applying powder for dusting an arthropod-infested area include mechanical dusters, hand shakers, or self-treatment devices used for livestock. with

Example 2N

Edible bait with the following composition is prepared: Active ingredient from 0.1 to 1.095 -

Wheat flour 8090 -

Molasses from 19.9 to 1995 I«o)

All ingredients are thoroughly mixed and formed into baits of the desired shape, edible baits can be placed in various places, in residential or industrial premises, for example, in kitchens, hospitals or storage rooms, or outside premises infested with arthropods, for example, ants, locusts, cockroaches " or by flies to control arthropods by oral absorption. Example 21

Prepare a solution of the following composition:

Active ingredient 1595

Dimethyl sulfoxide 8595

The active ingredient is dissolved in dimethyl sulfoxide with stirring or heating, if necessary. This solution can be applied through the skin, by pouring on domestic animals infected with -1 arthropods, or after sterilization by filtering through a polytetrafluoroethylene membrane (pore size 0.22 μm), by parenteral injection, at a dose of 1.2 to 12 ml of solution per 100 kg body weight of the animal.

Ge) 50 Example 2)

I" Prepare a wettable powder of the following composition:

Active ingredient 5095

Eshuiap VSR Bor 29 Aegoziy B

GF) Seiye RE 4095 o ETuiap VSR is absorbed on Aegosia, which is then mixed with other ingredients and crushed in a hammer mill to obtain a wettable powder, which can be diluted with water to a concentration of 0.00195 to 295 per 60 weight of the active compound, and applied to the site , infested with arthropods, such as diptera larvae or plant nematodes, by spraying, or on domestic animals infected or at risk of infestation with arthropods, helminths or protozoa, by spraying or dipping, or by oral administration with drinking water, to control arthropods, helminths or protozoa. because Example 2K

Prepare a composition in the form of pills with delayed release from granules containing the following components in different percentages (similar to those described for the previous compositions), depending on the need:

Active ingredient

Density agent

An agent that provides a delayed release

binding

All thoroughly mixed ingredients are formed in the form of granules, which are pressed into capsules with a specific density of 2 or higher. they can be administered orally to ruminant pets so that they are retained in the reticulo-rumen (first part of the stomach) and provide a sustained, sustained release of the active compound 7/0 over a long period of time to control arthropod, helminth or protozoan infestations in ruminant pets.

Example 2.

You can prepare slow-release compositions in the form of granules, tablets, briquettes, etc. of the next syllable: y y

Active ingredient from 0.5 to 2595

Polyvinyl chloride from 75 to 9995

Dioctyl phthalate (plasticizer)

All components are mixed and then added to the desired shape in appropriate molds by melt extrusion or pressing. These compositions can be used, for example, to add to stagnant water or to make collars or ear patches to attach to pets for pest control due to slow release.

Example 2M

Prepare water-dispersible granules of the following composition: p

Active ingredient 8595 (max) o

Polyvinylpyrrolidone Bo

Attapulgite clay

Sodium lauryl sulfate 290 M

Glycerin 290 Geo)

All ingredients are mixed in the form of a 4595 suspension with water and wet-milled to a size of 4 microns, then spray-dried to remove water. M

Although the present invention has been disclosed in various preferred embodiments, it should be clear to those skilled in the art that various modifications, substitutions, omissions, and changes may be made without departing from the scope of the invention. Accordingly, d) it is necessary to consider that the scope of this invention is limited only by the scope of the applied claims, including its equivalents.

Claims (30)

" 40 The formula of the invention shsh s h 1. 1-arylpyrazole of the formula (I) and ny "(U ee), Mn. F - m - Kk, o M s» 70 more eE T» ge 'Ez where: Ku - H or halogen; F) each of Co» and Ka, which are the same or different, is H, halogen or alkyl; ka Kz - halogen, haloalkyl, haloalkoxy or Kio5(O) t; Kb - lower alkyl, haloalkyl, alkenyl or alkynyl; or a cycloalkyl ring having from 3 to 5 carbon atoms; 2 - hydrogen, halogen, alkyl, formyl, -C(O)alkyl, haloalkyl; alkenyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, alkoxyalkylideneamino, 1H-pyrrol-1-yl, 1H-pyrazol-1-yl, amino, KeMH- or K7PvM; each of the radicals Ko, K7 and Kv, which may be the same or different, represent alkyl-5(O) p 65 formyl, alkynyl having from C to b carbon atoms, alkoxycarbonyl, alkylthiocarbonyl or aryl; or alkyl, alkenyl, having from 3 to 6 carbon atoms, or -C(O)alkyl, where alkyl and alkenyl parts are optionally substituted by one or more Co radicals; or radicals K";7 and Kd are combined in such a way that together they form a divalent radical containing from 4 to b atoms in the chain, and this divalent radical is alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, preferably with the formation of morpholine, pyrrolidine, piperidine or piperazine ring; Co - cyano, nitro, alkoxy, haloalkoxy, Kio5(O)d-, -C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, -СО2Н, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl; 70 Ko - lower alkyl or lower haloalkyl; t, n, p and a are equal to 0, 1 or 2; M - С-halogen, С-СН3, С-СНоР, С-СНСИ, С-МО" or M; or a salt of a compound of formula (I) acceptable as a pesticide, with the exception of 1-arylpyrazoles of formula (I), in which: Kb is haloalkyl, and 27 is hydrogen, 1H-pyrrol-1-yl, amino or KeMH, where Ke is formyl, alkynyl having from 3 to 6 carbon atoms, alkoxycarbonyl, alkyl, alkenyl having from 3 to 6 carbon atoms, or -C(O) alkyl, where the alkyl part is optionally substituted by one or more Co radicals, where Co is a halogen and other symbols have the above meanings. 2. The compound of formula (I) according to claim 1, in which Kz is halogen, haloalkyl or haloalkyl. 3. The compound of formula (I) according to claims 1 or 2, in which Kb is alkyl. 4. The compound of formula (I) according to claims 1-3, in which 2 is amino, KeMH- or KURvM-. 5. Compound of formula (I) according to claim 1, in which: Ku is RE, SI, Vgabo is H; E" and E. represent H; c Kz is -SEz, -OSEz, -SNE»z, -(O)ySEz, -SESI», -SE»SI, -OSE»SI, -OSESI», SI, Vg or E; Kb - methyl or ethyl; (8) 7 - H, halogen (E, SI, Bi), C--C3-alkyl, C--C3-haloalkyl, Co-C3-alkenyl; or amino, -MNKe or -MK7Ka, where each of the radicals Kv, K; and Ka, which are the same or different, are C.4-C3-alkyl, C3-alkenyl or -C(O)alkyl, in which the alkyl and alkenyl parts are unsubstituted or substituted by cyano, alkoxy, alkyl-5(O) p -, nitro, "g" with alkoxycarbonyl, -C(O)alkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, -СО5Н, hydroxy or halogen (НЕ, СИ, Вг); and and M are SSI, SE, SVg or M. i- 6. The compound of formula (I) according to claim 1, in which: Ku is Si or Vg; in. E" and E. represent H; so Ez is -SEz, -OSE" or SI; Kb - methyl or ethyl; 2 - H, halogen (P, CI, Bg), C4-C3-alkyl, C4-C3-haloalkyl, Co-C3-alkenyl; or amino, -MNK; or -MK7Rav, where each of the radicals Kv, K; and Ka, which are the same or different, are C1-C3-alkyl, C3-alkenyl or -C(O)alkyl, in which the alkyl and alkenyl parts are unsubstituted or substituted by cyano, alkoxy, alkyl-b(O) p -, nitro, C with alkoxycarbonyl, -C(O)alkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, -СО5Н, hydroxy or halogen (PE, SI, Bg); and M is SSI, SVg or M. y?" 7. The compound of formula (I) according to claim 1, in which: Ki. is Si or Vg; E" and KE; are H; b Ez is -SEz, -OSE" or SI; Kb - methyl or ethyl; Sh- 7 - H or an amino group; and -I M is SSI, SVg or M. 8. The compound of formula (I) according to claim 1, in which: and Ku is Si or Vg; i" E" and E. represent H; Ez is -SEz, -OSE" or SI; Kb - methyl or ethyl; 5B 7 - H or an amino group; and M is SSI, SVg or MF) 9. The compound of formula (I) according to claim 1, in which the 1-aryl group is selected from: 2,6b-dichloro-4-trifluoromethylphenyl, ka 2,6-dichloro-4-trifluoromethoxyphenyl, 2-bromo-6-chloro-4 -trifluoromethylphenyl, 2-bromo-6-chloro-4-trifluoromethoxyphenyl, 2,6-difluoro-4-trifluoromethylphenyl, 2-chloro-4--rifluoromethylphenyl, bo 2,b-dichloro-3-methyl-4-trifluoromethylphenyl, C -chloro-5-trifluoromethyl-2-pyridinyl, 3-chloro-5-trifluoromethoxy-2-pyridinyl, 3,5-dichloro-2-pyridinyl, 2,6-dichloro-4-bromophenyl, 2,4,6-trichlorophenyl , 2-bromo-6-fluoro-4-difluoromethylphenyl, 2-chloro-6-fluoro-4-trifluoromethylphenyl, 2,6-dibromo-4-trifluoromethylphenyl, 2,6-dibromo-4-trifluoromethoxyphenyl or 2-bromo-4 -trifluoromethylphenyl. 10. The compound of formula (I) according to claim 1, in which group 7 is a group: acetylamino, amino, 2-n-butoxypropionylamino, b5 Methyl, hydroxyacetylamino, ethyl, 3-ethylsulfinylpropylamino, bromine, formylamino, chlorine, methylamino, ethylamino, 2 -hydroxyethylamino, 2-methoxyethylamino, methylsulfonylamino, 2-ethylsulfonylethylamino, 4-Methoxybenzoylamino, 2-cyanoethylamino, 4-methoxybenzylamino, 2-methylthioethylamino, 2-aminocarbonylethylamino, 2-methylsulfinylethylamino, 3-methoxycarbonylpropylamino, 2-ethylsulfinylethylamino, 2-methylsulfonylethylamino, cyanomethylamino, 2-ethylthioethylamino, aminocarbonylmethylamino, 2-nitroamino, dimethylamino 2-acetylethylamino, methylcarbonylmethylamino, methoxycarbonylamino or ethoxycarbonylamino. 11. The compound of formula (I) according to claim 1, in which the -5(0) 0K5 group is methylthio, methylsulfinyl, methylsulfonyl, ethylsulfinyl, ethylsulfonyl, ethylthio, cyclopropylsulfinyl, cyclopropylthio, cyclopropylsulfonyl, isopropylsulfonyl, isopropylsulfonyl or isopropylthio. 70 12. The compound of formula (I) according to claim 1, selected from: 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthiopyrazole-3-thiocarboxamide; 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole-3-thiocarboxamide; 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfonylpyrazole-3-thiocarboxamide; 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide; 5-amino-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide; 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole-3-thiocarboxamide; 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole-3-thiocarboxamide; 5-amino-1-(2-bromo-6-chloro-4-trifluoromethylphenyl)-4-ethylsulfinylpyrazole-3-thiocarboxamide or 5-amino-1-(2,6-dichloro-4-trifluoromethoxyphenyl)-4-ethylsulfinylpyrazole- 3-thiocarboxamide. 13. The compound of formula (I) according to claim 1, which is 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole-3-thiocarboxamide or 4-dichlorofluoromethylsulfonyl-1-(2,4, 6-trichlorophenyl)pyrazole-3-thiocarboxamide. 14. Pesticidal composition, which contains an effective amount of the compound of formula (I) according to any one of claims 1-13 or its salt acceptable as a pesticide in combination with an inert carrier acceptable in general agricultural terms. 15. Pesticidal composition according to claim 14, which contains about 0.05-95 wt. 956 compounds of formula (1). and) 16. Pesticidal composition according to claim 14, which contains about 0.00005-9Omas. 95 compounds of formula (1). 17. The method of combating pests in the focus of infection, which consists in applying to the specified focus an effective amount of the compound of formula (I) according to any of claims 1-13 or its acceptable as "g of a pesticide salt or composition according to any which of claims 14-16. 18. The method according to claim 17, in which the indicated pests are insects. and 19. The method according to claim 17, in which the indicated insects are sucking insects. M 20. The method according to claim 17, in which the indicated focus of infection is an area sown with crops. 21. The method according to claim 17, in which the indicated compound is applied to the indicated focus of infection in the amount of about 5 g to about 1 kg/ha. co 22. The method according to claim 17, in which the indicated source of infection is an animal. 23. The method according to claim 22, in which the indicated compound is applied to the indicated focus of infection in an amount of about 0.1-20 mg per kg of animal body weight per day. 24. The method of combating vertebrate pests, which includes the application to the animal of 1-arylpyrazole " of formula (I) according to claim 1 or its acceptable salt as a pesticide in a single dose of 0.1-100 mg per kg of the animal's body weight, with or without in doses of 0.01-20 mg per kg of animal body weight daily. 25. The method of obtaining the compound of formula (I) or its salt acceptable as a pesticide according to claims 1-13, which includes;" the interaction of the compound of the formula (II) KA(O, CM, (1) Me Y M i M -I - i | tm oz 7 in de-v, i» and Kz de Ki, Ko, Kz, Ka, Kv, M i 2 defined according to claim 1, with alkali or alkaline earth metal hydrosulfide. 22 26. The method of obtaining the compound of formula (I) or its salt acceptable as a pesticide according to claims 1-13 Ф) име) 60 b5 With ШЧО) keBO), МН, Щ and Кк, | that M dO KE R and Ez de Ki, Ko, Kz, Ka, Kv, M and 2 are determined according to claim 1, and n is equal to 1 or 2 by oxidation of compounds corresponding to formula (I), in which n is equal to 0 or 1; 19 or when 7 is a -C(O)alkyl group, - oxidation of the corresponding compound of the formula (MIP): C ; (MIP) KeV(O), Mn, an M t Kk: M K., - WHAT and from dev, o) Ke Kz where Ku, K», Kz, Ku, Kb and M are defined according to claim 1, and K.) - alkyl. "AND 27. The method of obtaining the compound of formula (I) or its salt acceptable as a pesticide according to claims 1-13 со 8 ЧО) ча кеBO), МН, В m" (Се) Кк, | that M le e « and ge shi s Ez: z" where Ku, Ko, Kz, Ka, Kv and M are defined according to claim 1, and 7 is KeMH-, where K" is ethyl substituted in position 2 by the Ko radical, where Ko is cyano, nitro, -B(O) aKcho, -C(O)alkyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl, by alkylation of the corresponding compound of the formula (I), b where 2 is an amino group, by the compound of the formula (I): Co-СНеСН»5, (PP) - where Ko has the above value; -1 or when Ku, K", Kz, Ka, Kb and M are defined according to claim 1, and 7 is -MNK" or -MK7Ra, where Kb, K7 and Kz represent alkyl or haloalkyl, optionally substituted by one or more radicals K o, by alkylation of the corresponding o compound of formula (I), where 2 is an amino group, by a compound of formula (IM): T» K44-U, (M) where K.i1 is alkyl or haloalkyl, neoob necessarily substituted by one or more Ko radicals, and MU is a leaving group I. 28. The method of obtaining a compound of the formula (I) or its salt acceptable as a pesticide according to claims 1-13, where 7 is alkoxycarbonyl, by esterification of the corresponding compound of the formula (I), where 7 is a carboxyl group, (F) with an alcohol of the formula (M): GP K.2OHN, (M) de K." - alkyl; in or where 7 is alkylthiocarbonyl, by esterification of the corresponding compound of formula (I), where 7 is a carboxyl group, a thiol of formula (MI): KoZN, (MI) de K." - alkyl 29. The method of obtaining the compound of formula (I) or its salt acceptable as a pesticide according to claims 1-13, 65 where 7 is KizCH(СИ)CH»-, where K.z is alkyl, by diazotization of the corresponding compound of formula (I), in which 7 is an amino group, followed by reaction with a compound of the formula (MI): KisSnNeSsN", (MII) in the presence of a copper salt. 30. The method of obtaining the compound of formula (I) or its salt acceptable as a pesticide according to claims 1-13, where 7 is KizCHNeCH- and K.z - alkyl, by dehydrochlorination of the corresponding compound of formula (I), in which 2 is K-ZCH(СИ )СН»5-. Official bulletin "Industrial Property". Book 1 "Inventions, useful models, topographies of integrated microcircuits", 2004, M 7, 15.07.2004. State Department of Intellectual Property of the Ministry of Education and Science of Ukraine. s o " so cha cha (Se) shi s ;" (22) -I -I o 50 s» F) ime) 60 b5