RU2063688C1 - Pyrrol derivatives, insecticide-acaricide composition and a method of struggle against insects and ticks - Google Patents

Abstract

FIELD: organic chemistry. SUBSTANCE: products: derivatives of pyrroles of the formula (I)

where X - halogen, thiocyanato, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, halide-C₁-C₂-alkylthio, halide-C₁-C₄-alkylsulfonyl; R' - hydrogen, halogen, amino, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, trifluoromethylcarbonylamino, C₁-C₄-alkylthiomethyladepimino; R^2′ - cyano, formyl, C₁-C₄-alkyl, difluoromethyl; R³ - hydrogen. halogen, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, thiocyanato, halide- C₁-C₄-alkylthio, bis-(C₁-C₄-alkyl)-methyl; X₁ - hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl; X₄ - halogen, hydrogen, C₁-C₄-alkyl; Y - halogen, halogenalkyl-C₁-C₄-halogenalkoxy-C₁-C₄-alkyl, methoxycarbonyl; X₂ and X₃ - hydrogen, and insecticide-acaricide composition and a method of struggle against insects and ticks. Synthesized compounds were used in agriculture for plant protection. ???EFFECT: improved method of synthesis. 6 tbl

Description

 The present invention relates to new compounds belonging to the class of pyrroles. The present invention relates to the use of these compounds in agriculture, especially as pesticides, for the control of arthropods, preferably as insecticides and anaricides, the present invention also relates to agrochemical compositions used to control arthropods, especially insects and arachnids.

 Many pyrazoles (heterocyclic compounds containing two nitrogen atoms) are well known as insecticides. Some compounds containing a pyrrole group (compounds containing one nitrogen atom) are also known as insecticides. However, they usually also contain another chemical group, which is well known to have insecticidal properties as such, for example a pyrethroid group or a carbamate group, or some kind of organophosphorus group. So, for example, in the patent GB N 2189242 simple substituted pyrrole derivatives are already described as agrochemical compounds, but serving as fungicides.

в которой Х галоген, тисцианато, С₁ С₄-алкилтио, С₁ - С₄-алкилсульфинил, С₁ С₄-алкилсульфонил, галоид C₁ C₂-алкилтио, содержащий 3-5 различных атомов галогена, галоид - C₁ C₂-алкилсульфонил, содержащий от 3 до 5 атомов галогена, R¹ водород, галоген, амино, С₁ С₄-алкилтио, С₁ - С₄-алкилсульфинил С₁ С₄ алкилсульфонил, трифторметилкарбониламино, С₁ С₄ алкилтиометилиденимино, R² циано, формил, С₁ С₄- алкил, дифторметил. R³ - водород, галоген, С₁ С₄ алкилтио, С₁ С₄ алкилсульфинил. С₁ С₄ алкилсульфонил, тиоцианато, галоид С₁ C₄ алкилтио, содержащий 3 атома галогена, бис(С₁ - С₄- алкил) метил. Х₁ водород, галоген, С₁ С₄ - алкил, С₁ С₄ алкилтио, С₁ С₄ алкилсульфинил, Х₄ галоген, водород, С₁ С₄ алкил, Y галоген, галогеналкил С₁ С₄, галогеналкокси С₁ С₄, метоксикарбонил, X₂ и X₃ водород, если Х₄ и Х₁- водород, а X галоген, то R₂ имеет значение, отличное от X.The present invention is the creation of new compounds with insecticidal and acaricidal activity, allowing to expand the range of insectacaricidal compositions for pest control,
The problem is solved by new derivatives of pyrroles of formula I

in which X is halogen, tiscyanato, C ₁ C ₄ -alkylthio, C ₁ - C ₄ -alkylsulfinyl, C ₁ C ₄ -alkylsulfonyl, halogen C ₁ C ₂ -alkylthio containing 3-5 different halogen atoms, halogen - C ₁ C _2- alkylsulfonyl containing from 3 to 5 halogen atoms, R ¹ hydrogen, halogen, amino, C ₁ C ₄ -alkylthio, C ₁ - C ₄ -alkylsulfinyl C ₁ C ₄ alkylsulfonyl, trifluoromethylcarbonylamino, C ₁ C ₄ alkylthiomethylidenimino, R ² cyano, formyl, C ₁ C ₄ - alkyl, difluoromethyl. R ³ is hydrogen, halogen, C ₁ C ₄ alkylthio, C ₁ C ₄ alkylsulfinyl. C ₁ C ₄ alkylsulfonyl, thiocyanato, halo C ₁ C ₄ alkylthio containing 3 halogen atoms, bis (C ₁ - C ₄ - alkyl) methyl. X ₁ hydrogen, halogen, C ₁ C ₄ - alkyl, C ₁ C ₄ alkylthio, C ₁ C ₄ alkylsulfinyl, X ₄ halogen, hydrogen, C ₁ C ₄ alkyl, Y halogen, haloalkyl C ₁ C ₄ , haloalkoxy C ₁ C ₄ , methoxycarbonyl, X ₂ and X ₃ hydrogen, if X ₄ and X ₁ is hydrogen and X is halogen, then R ₂ has a value other than X.

в которой X представляет собой R⁵S(0)_n, где n равно О,1 или 2 и R⁵ представляет собой CH₃, СF₃, СF₂Сl, СFCl₂, СF₂ Вr, СHF₂ или СHClF;
R² представляет собой цианогруппу; R¹ представляет собой Н, F, Сl или Вr.More specific compounds of the general formula (I), which are preferred and of particular interest, are compounds
A) Compounds of formula (II) with high insecticidal activity

in which X represents R ⁵ S (0) _n , where n is O, 1 or 2 and R ⁵ is CH ₃ , CF ₃ , CF ₂ Cl, CFl ₂ , CF ₂ Br, CHF ₂ or CHClF;
R ² represents a cyano group; R ¹ represents H, F, Cl or Br.

Of these, the following are preferred.
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (trifluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4- (trifluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) - 2-chloro-3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (chlorodifluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-chloro-difluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (chlorodifluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (trifluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo3-cyano-4- (trifluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (chlorodifluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (chlorodifluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4 - (dichlorofluoromethylsulfonyl) -5-bromopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (chlorodifluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4 - (dichlorofluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2-chloro-4-trifluoromethylphenyl) -2-chloro-3-cyano - 4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2-chloro-4-trifluoromethylphenyl) -2-chloro-3-cyano -4- (dichlorofluoromethylsulfinyl) pyrrole;
1- (2-chloro-4-trifluoromethylphenyl) -2-bromo-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylthio) -5-methylthiopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (bromodifluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (bromodifluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (bromodifluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2- chloro-3 cyano-4 - (methylsulfinyl) pyrrole or
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (methylsulfonyl) pyrrole.

C) Other compounds of formula (II) with high insecticidal activity, in which
X is R ⁵ S (0) _n , where n is O, 1 or 2, R ⁵ is CH ₃ , CF ₃ , CF ₂ Cl or CFFC ₂ ;
R ⁵ represents a cyano group;
R ¹ represents H, F, Cl, Br, or NH ₂ ;
R ³ represents H, F, Cl, Br, CF ₃ or CN;
X ₁ represents H or Cl;
Y represents CF ₃ or CF ₃ O.

The compounds of this invention, which are preferred for their insecticidal activity, are as follows
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (trifluoromethylsulfonyl) pyrrole;
1- (1,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (trifluoromethylsulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfinyl-5-bromopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfonyl-5-bromopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (trifluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-bromo-3-trifluoromethylthio-4-cyano-5-chloropyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) - 2 - [(trifluoromethyl) carbonylamino] -3-trifluoromethylthio-4-cyano-5-chloropyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2 - (methylcarbonylamino-3-trifluoromethylthio-4-cyano-5-chloropyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino3-trifluoromethylthio-4-cyano-5-chloropyrrole;
1- (2-chloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-dichlorofluoromethylthio-4-cyano-5-chloropyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2,4-bis (trifluoromethylthio) -3-cyano-5-aminopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-bromopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole;
1- (4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-bromopyrrole;
1- (2-chloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-bromopyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3--cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethanesulfinyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-2-chloro-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole or 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfonyl ) pyrrole.

C) Compounds of formula (I) which have surprisingly high acaricidal activity, in which
X represents a halogen atom or a group R ⁵ S (O) _n , where n is 0.1 or 2, and R ⁵ represents alkyl, preferably alkyl with a content of 1-4 C atoms, haloalkyl, preferably trihalomethyl, especially preferably with halogen from F ₁ , Cl or Br, or a combination thereof, for example CF ₃ , CCl ₃ , CF ₂ Cl, CFl ₂ or CF ₂ Br alkenyl, or haloalkenyl;
R ¹ and R ³ each represents a hydrogen atom;
R ² represents a cyano group;
Y represents a hydrogen atom or a halogen atom, preferably Cl or Br;
X ¹ , X ² , X ³ and X ⁴ are individually selected from the group consisting of hydrogen, halogen, alkyl with a content of 1-3 C atoms, alkoxy with a content of 1-3 C atoms, and alkylthio with a content of 1-3 C atom; X ¹ and X ⁴ each are preferably H, F, Cl, Br or CH ₃ , and X ² and X ³ each represent hydrogen.

Of these compounds, the following are more preferred.
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (chlorodifluoromethylthio) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (trifluoromethylthio) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (chlorodifluoromethylthio) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (chlorodifluoromethylsulfinyl) pyrrole.

1- (2,4,6-trichlorophenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole;
1- (2,4,6-trichlorophenyl-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole;
1-4-bromo-2,6-dichlorophenyl) -3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole;
1- (2,4,6-trichlorophenyl) - 3-cyano-4- (trifluoromethylthio) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (trifluoromethylsulfinyl) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (trifluoromethylsulfonyl) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (trichloromethylthio) pyrrole;
1- (2,4-dichlorophenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4-chloropyrrole;
1- (2,4,6-trichlorophenyl) -3-cyano-4- (chlorodifluoromethylsulfonyl) pyrrole;
1- (2,6-dichlorophenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (trifluoromethylsulfinyl) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (trifluoromethylsulfonyl) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (chlorodifluoromethylsulfinyl) pyrrole;
1- (4-bromo-2,6-dichlorophenyl) -3-cyano-4- (chlorodifluorofetylsulfonyl) pyrrole;
1- (4-bromo-2,6-dimethylphenyl) -3-cyano-4- (trifluoromethylsulfinyl) pyrrole;
1- (4-bromo-2,6-dimethylphenyl) -3-cyano-4- (trifluoromethylsulfonyl) pyrrole or
1- (4-bromo-2,6-difluorophenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole.

E) Other preferred compounds of formula (I) are compounds of formula (I) in which:
R ¹ represents a hydrogen atom or a halogen atom such as chlorine or bromine;
R ² represents a cyano group;
X represents a haloalkylthio group or a haloalkylsulfinyl or haloalkylsulfonyl group, preferably CF ₃ S (O) _n , in which n is O, 1 or 2;
X ¹ and X ⁴ have values lower than a hydrogen atom;
X ² and X ³ each represent a hydrogen atom;
Y represents haloalkyl or haloalkoxy.

 The subject of this invention covers new insecticides and acaricides belonging to the pyrrole family.

 The compounds of the invention are very active compounds. These and other products of the present invention are obtained in whole or in part using the new compounds as defined below.

 Compounds of general formula (I) are prepared using methods previously known (for example, methods previously known and described in the chemical literature), usually the formation of a pyrrole ring is carried out where necessary by replacing the substituents. In addition, compounds of general formula (I) can be chemically converted to other compounds of formula (I) by methods known to those skilled in the art.

Typical Compounds of the Invention
Typical pyrrole compounds (RPCs) encompassed by this invention are compounds of formula (I) wherein R ² is a cyano group and other substituents are as shown in Table 1 (RPCN 1-389)
Other specific typical pyrrole compounds (RPC) encompassed by this invention are compounds of formula (I) in which X ² and X ³ are hydrogen, X ¹ and X ⁴ are chlorine, Y is CF ₃ and X, R ¹ , R ² and R ³ have the meanings given in table 2 (RPC N 390 491).

 The following examples 1-22 further illustrate the synthesis methods and physical characteristics of the insecticidal compounds (and their chemical intermediates) corresponding to the present invention.

 Example 1

A solution of 910 mg (2.07 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylthiopyrrole (prepared according to the procedure described in example 2) and 492 mg of 80% - methachloroperbenzoic acid (394 mg, 2.28 mmol) in 25 ml of chloroform is stirred at room temperature for one and a half hours and then heated under reflux overnight. An additional 45 mg (0.21 mmol) of methachloroperbenzoic acid was added and heating under reflux continued for one hour. Then the heating is stopped, and the reaction mixture is diluted with dichloromethane and washed with an aqueous solution of sodium bicarbonate. The organic layer is dried over anhydrous sodium sulfate (MgSO ₄ ) and concentrated under reduced pressure, resulting in a colorless solid precipitate. This process is repeated in order to obtain a total of 950 mg of product, which is chromatographed on silica gel, eluting with a dichloromethane hexane mixture (2: 1 v / v). The first fractions contained 310 mg (24%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano4-trifluoromethylsulfonylpyrrole (Example 1) as a colorless solid. After recrystallization from hexane-ethyl acetate, 240 mg of sulfone are obtained in the form of colorless needles, with a melting point of 198 ^o C.

 Example 2

At the end of the process described in example 1, the chromatographic separation of the product continues. In the last fractions of chromatographic separation, 600 mg (48%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) 2-chloro-3-cyano-4-trifluoromethylsulfinylpyrrole (Example 2) is obtained as a colorless solid. After recrystallization from toluene - hexane 3OO mg of sulfoxide is obtained in the form of a colorless powder with a melting point of 152 154.5 ^o C.

 Example 3A and 3B.

Examples 1 and 2 were repeated using 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylthio-5-bromopyrrole as the starting material obtained according to the process described in example 5. The compound of example 3A is 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfinyl-5-bromopyrrole. This compound is obtained by following the procedure similar to the description of Example 2. It has a melting point of about 123 ^° C. The compounds of Example 3B are 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfonyl -5-bromopyrrole. This compound, obtained by the procedure analogous to the description of Example 1, has a melting point of about 113 ^° C.

 Example 4

A solution of 3 g (6.6 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (prepared according to the procedure described in example 8) in 50 ml of dry tetrahydrofuran, stirred under nitrogen and 3.9 ml (3.4 g, 33 mmol) of tert-butyl nitrile are added. After 30 minutes, the reaction mixture was heated under reflux for about one hour, then concentrated under reduced pressure, and the result was 3.69 g of solid precipitate. This procedure is repeated in order to obtain a total of 4.07 g of solid precipitate, which is chromatographed on silica gel, eluting with dichloromethane hexane (in a volume ratio v / v 1: 1), and the result is 2.9 g ( 91%) 1- (2-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylthiopyrrole (Example 4) as a colorless solid. After recrystallization on a mixture of hexane-ethyl acetate, 1.87 g of product is obtained in the form of a colorless powder with a melting point of about 137 ^o C.

 Example 5

To a heterogeneous mixture, 2.4 g (5.28 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (prepared according to the procedure described in the example 8) in 40 ml of bromoform in an inert atmosphere, 0.94 ml (820 mg, 7.92 mmol) of tert-butyl nitrile are added. After stirring for 15 minutes at room temperature, the reaction mixture was concentrated under reduced pressure to give 3.9 g of a precipitate. This precipitate is combined with the product obtained in the previous reaction, 300 mg of the same pyrrole starting material. This crude product was chromatographed on silica gel, eluting with a 4: 1 (v / v) hexane adichloromethane mixture. During this separation, 1.72 g (56%) of 1- (2,6-dichloro-4-trifluoromethyl-phenyl) -2-bromo-3-trifluoromethyl-thio-4-cyano-5-chloropyrrole (Example 5) is liberated, which recrystallized from hexane, and the result is 780 mg of the product as a colorless solid with a melting point of 92 ^o C.

 Example 6

A solution of 1.91 g (4.21 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (prepared according to the procedure described in example 8) , 77 mg (0.63 mmol) of 4-dimethylaminopyridine and 20 ml of pyridine in an inert atmosphere are cooled at 0 ^{° C.} and 1.01 ml (1.50 g, 7.14 mmol) of trifluoroacetic acid anhydride are added to it. The reaction mixture is stirred at 0 ^{° C.} for 1 hour and at 20 ^{° C.} for 4 hours, then an additional 0.30 ml (2.1 mmol) of trifluoroacetic anhydride is added. After the reaction, the reaction mixture is diluted with dichloromethane for 24 hours and concentrated. The precipitate is washed with an aqueous HCl solution, then with water and recrystallized from hexane-ethyl acetate, and as a result, 860 mg (37%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2- (trifluoromethylcarbonylamino) -3-trifluoromethylthio- 4-cyano-5-chloropyrrole (example 6) in the form of a pale green solid with a melting point of about 190 ^o C.

 Example 7

A mixture of 1.50 g (3.3 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (obtained as described in Example 8), 0, 10 g of 4-dimethylaminopyridine, 0.33 ml (0.32 g, 4.01 mmol) of pyridine, 0.31 ml (0.34 g, 4.3 mmol) of acetyl chloride and 10 ml of acetonitrile is stirred for 4 days at a temperature 20 ^o C and 1 day when heated under reflux. Then, an additional 0.03 ml of acetyl chloride is introduced, and heating under reflux continues for another day, after which the reaction mixture is cooled, diluted with dichloromethane and sequentially distributed during treatment with 1.1 in HCl and saturated aqueous sodium bicarbonate. The organic layer is dried over anhydrous magnesium sulfate and evaporated to give 1.42 g of a beige solid. Chromatographic separation on silica gel, eluting with hexane-ethyl acetate 4: 1 (v / v), followed by recrystallization from ethanol, gives 460 mg (29%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2 -methylcarbonylamino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (example 7) in the form of colorless needles with a melting point of 216 ^o C.

 Example 8

A mixed solution of 1.50 g (3.57 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole (obtained according to the procedure described in example 13) in 15 ml ethyl ether is cooled to -20 ^{° C.} in an inert atmosphere, and a solution of 0.29 ml (0.48 g, 3.6 mmol) of sulfuryl chloride in 15 ml of anhydrous ethyl ether is added dropwise. Then the reaction mixture is heated to 20 ^o C and stirred for 2.5 days, after which an additional 0.03 ml (0.4 mmol) of sulfuryl chloride is introduced and stirring continues for one more day. An additional 0.03 ml of sulfuryl chloride is added and after another day the reaction mixture is cooled with 28 ml of a 10% aqueous solution of potassium carbonate. Phase separation occurs and the aqueous layer is extracted with ether. Then the ether layers are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated, resulting in 1.56 g of a tan solid. This crude product is chromatographed on silica gel eluting with a dichloromethane hexane mixture in a ratio of 2: 1 (v / v), and as a result 1.30 g (80%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) - 2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (Example 8) as a pale pink solid. After recrystallization from cyclohexane, 810 mg of product is obtained in the form of whitish needles with a melting point of about 176 ^o C.

 Example 9

A procedure similar to the description of Example 8 is carried out, with the difference that 1- (2-chloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole (with a melting point of 169 ^{° C.} ) is used as a reagent, which obtained according to the method described in example 13. The final product is 1- (2-chloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano-5-chloropyrrole (example 9) with a melting point of about 146 ^o FROM.

 Example 10

The procedure is carried out analogously to example 8 with the difference that 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-dichlorofluoromethylthio4-cyanopyrrole (melting point 202 ^{° C.} ) is used as a reagent, as described in Example 13. The final product is 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-dichlorofluoromethylthio-4-cyano-5-chloropyrrole (Example 10) with a melting point of about 207 ^° C.

 Example 11

The compound 1- (2,6-dichloro-4-trifluoromethylphenyl) -2,4-bis- (trifluoromethylthio) -3-cyano-5-aminopyrrole (Example 11) has a melting point of 161 ^{° C.} and is obtained as described in Example 13 (first compound) using an excess of trifluoromethanesulfenyl chloride.

 Example 12

To a cold (0 ^° C) solution of 1.53 g (3.60 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole (obtained by the method described in the example 13, with a melting point of about 182 ^° C) in 15 ml of pyridine, a solution of 1.46 g (3.6 mmol) of 80% pyridine bromide perbromide in 15 ml of pyridine is introduced in an inert atmosphere. After 30 minutes, the reaction mixture was poured into cold (O ^o C) ethyl ether and the precipitate formed in this way was removed by filtration. The filtrate is washed with an aqueous solution of HCl, an aqueous solution of NaOH and water. The organic layer is dried over anhydrous magnesium sulfate and evaporated to give 1.34 g of a brown solid. This product is combined with 230 mg of the product from an earlier reaction, 300 mg (0.7 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) 2-amino-3-trifluoromethylthio-4 cyanopyrrole and 0.29 g of 80 % pyridine bromide perbromide. These combined products are chromatographed on silica gel eluting with hexane-ethyl acetate 4: 1 (v / v) to give 1.31 g (73%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2 -amino-3-trifluoromethylthio-4-cyano-5-bromopyrrole (Example 12) as a white solid. After recrystallization from a mixture of hexane / ethyl acetate, 910 mg of this product are obtained in the form of colorless needles with a melting point of about 16O ^° C.

 Example 13

A mixed solution of 2.00 g (6.25 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-4-cyanopyrrole in 60 ml of dichloromethane, prepared as described below, is cooled in an ice bath and introduced into in the form of a slow stream of 10 ml of a cold (-78 ^° C) dichloromethane solution containing 0.55 ml (0.85 g, 6.2 mmol) of trifluoromethanesulfenyl chloride. After stirring at 0 ^{° C.} for two hours, a stream of nitrogen was passed through the reaction mixture for one hour. After distribution during processing with saturated aqueous sodium bicarbonate and water, drying over anhydrous magnesium sulfate and concentration in vacuo, 3.14 g of a light brown solid are obtained. This product is chromatographed on silica gel, eluting with a dichloromethane-hexane mixture of 3: 2 (v / v), and the result is two colorless solid samples in the amount of 900 and 950 mg. These products are recrystallized from chloroform, and the result is respectively 680 and 630 mg of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole (example 13) with a melting point of about 182 ^o FROM.

 The reagent used in this process is obtained as follows.

A solution of 4.64 g (14.5 mmol) of 1 - [(2,6-dichloro-4-trifluoromethylphenyl) amino] -2,3-dicyanopropane and 2.02 ml (1.47 g, 14.5 mmol) of triethylamine in 30 ml of benzene is heated under reflux overnight and then concentrated in vacuo. The precipitate was partitioned between ethyl ether and water, and the ether layer was dried over anhydrous magnesium sulfate and concentrated, resulting in 3.79 g of a light brown solid. After recrystallization from ethanol-water, 2.79 g (60%) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-4-cyanopyrrole with a melting point of about 176 ^° C are obtained.

The starting 1-aralamino-2,3-dipianopropene is prepared as follows: 20.5 g (0.140 mol) of the potassium salt of formyl succinonitrile sample is dissolved in approximately 30 ml of water and acidified with concentrated hydrochloric acid. This product is extracted with ethyl ether, the ether extract is dried over anhydrous magnesium sulfate and evaporated, resulting in 3.87 g of a brown liquid product. This product is introduced into a solution containing 5.04 g (22 mmol) of 2,6-dichloro-4-trifluoromethylaniline and 40 mg of para-toluenesulfonic acid, monohydrate, in 50 ml of benzene. This heterogeneous reaction mixture is refluxed overnight with water separation. Then the reaction mixture is cooled and concentrated, and the result is 7.66 g of a yellow liquid. While stirring with hexane, 6.8 g (95%) of 1- [2,6-dichloro-4-trifluoromethylphenyl) amino] -2,3-dicyanopropene precipitated as a yellow solid. After recrystallization from ethanol / water, a product is obtained with a melting point of 1O1 ^o C.

 Examples 14A and 14B.

To a suspension of 1.17 g (3.30 mmol) of 1- (4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole and 0.46 ml (0.34 g, 3.3 mmol) of triethylamine in 20 mi chloroform, cooled to 20 ^o With, enter a solution of 0.19 ml (0.59 g, 3.7 mmol) of bromine in 5 ml of chloroform. The reaction mixture is stirred at a temperature of -20 ^o C for 1 hour and then heated to 0 ^o C. Then another 0.04 ml (0.13 g, 0.8 mmol) of bromine is introduced, and after additional stirring for 15 minutes, the reaction the mixture is diluted with dichloromethane and partitioned between water and saturated aqueous sodium bicarbonate. The organic layer is dried over anhydrous magnesium sulfate and concentrated to give 1.11 g of a brown solid. This material is combined with the product from the previous reaction 1.00 g (2.8 mmol) of 1- (4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole and 0.15 ml of bromine. After chromatographic separation on silica gel, eluting with a 3: 1 (v / v) dichloromethane-hexane mixture, 1.40 g (52%) of 1- (4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyano- is obtained 5-bromopyrrole (Example 14A) as a yellow solid. After recrystallization from hexane-ethyl acetate, the product is obtained in the form of pale yellow plates with a melting point of about 175 ^o C.

1- (4-trifluoromethylphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole (Example 14B) with a melting point of about 152 ^{° C.} can be obtained from 1 - [(4-trifluoromethylphenyl) amino] -2,3-dicyanopropane according to the procedure described in example 13.

 Examples 15A and 15B.

1 - [(2-chloro-4-trifluoromethylphenyl) amino] -2,3-dicyanopropene is prepared according to the procedure described in example 13. This dicyanopropene is used to obtain 1- (2-chloro-4-trifluoromethylphenyl) -2-amino 3-trifluoromethylthio 4-cyanopyrrole (Example 15A) with a melting point of about 169 ^{° C.} obtained according to the procedure described in Example 13. This pyrrole is used to prepare 1- (2-chloro-4-trifluoromethylphenyl) -2-amino-3- trifluoromethylthio-4- cyano-5-bromopyrrole (Example 15B) with a melting point of about 157 ^{° C.} according to the procedure of Example 14.

 Examples 16A and 16B.

The 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-4-cyanopyrrole obtained according to Example 13 is treated with CFCl ₂ SCl according to the process described in Example 13 (which uses CF ₃ SCl) and the result is 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-amino-3-dichlorofluoromethylthio-4-cyanopyrrole (Example 16A) with a melting point of about 202 ^° C.

This compound is treated with 1-butyl nitrile according to the process of Example 4, and the result is 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylthio) pyrrole (Example 16B) with a melting point approximately 158 ^o C.

 Example 17

The last compound from example 16 chemically reacts according to the process described in examples 1 and 2 using hydrogen peroxide in trifluoromethyl peracetic acid (instead of meta-chloroperbenzoic acid) and the result is 1- (2,6-dichloro-4-trifluoromethylphenyl) -2- chloro-3-cyano-4- (dichlorofluoromethylsulfinyl) pyrrole (example 17) with a melting point of about 119 ^o C.

 Example 18

Carrying out the procedure according to example 17 using a double amount of hydrogen peroxide, the last compound of example 16 is converted to 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4- (dichlorofluoromethylsulfonyl) pyrrole (example 18) with a melting point of about 179 ^o C.

 Example 19

The first compound of example 16 is treated with tert-butyl nitrile according to the procedure described in example 4, and the result is 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-cyano-4- (dichlorofluoromethylthio) pyrrole (example 19) with a melting point 120 ^o C.

 Example 20

The compound of Example 19 is oxidized according to the procedure of Example 17, and the result is 1- (2,6-dichloro-4-trifluoromethylphenyl) cyano-4- (dichlorofluoromethylsulfonyl) pyrrole (Example 20) with a melting point of 150-152 ^° C.

 Examples 21A, 21B and 21C.

 1 - [(2,6-dichloro-4-trifluoromethoxyphenyl) amino] -2,3-dicyanopropene is obtained according to the procedure for preparing the latter compound of Example 13 using 2,5-dichloro-4-trifluoromethoxyaniline instead of 2,6-dichloro-4-trifluoromethylaniline.

 This compound is converted to 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-amino-4-cyanopyrrole according to the procedure for preparing the second compound of Example 13.

 This compound is converted to 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-amino-3-trifluoromethylthio-4-cyanopyrrole according to the procedure for preparing the first compound of Example 13.

This compound is converted to 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-amino-3- (trifluoromethylthio) -4-cyano-5-chloropyrrole (Example 21A) with a melting point of 196 197 ^{° C.} according to the procedure of Example 8 .

This compound is converted to 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4-trifluoromethylthiopyrrole (Example 21B) with a melting point of 172 ^{° C.} according to the procedure of Example 4. This compound is converted to 1- (2,6-Dichloro-4-trifluoromethoxyphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfonylpyrrole (Example 21C) with a melting point of 187 ^{° C.} according to the procedure of Example 18.

 Examples 22A, 22B and 22C.

A mixture of 2-chloro-4-chlorosulfenyl-3-cyano-1- (2 ', 6'-dichloro-4' trifluoromethyl-phenyl) pyrrole and 2-chloro-3-cyano-4-dichlorofluoromethylsulfonyl-1- (2 ', 6'-dichloro-4-trifluoromethylphenyl) pyrrole (47.77 g, 0.101 mol, 1.0 equiv.) Is dissolved in trifluoroacetic acid (190 ml) at 0 ^° C. To this solution is added dropwise 50% H ₂ O ₂ (10.8 ml, 0.106 mmol, 1.05 equiv.) The reaction mixture was stirred at 0 ^{° C.} for 7 hours and 15 minutes, then it was placed in the refrigerator (10 ^{° C.} ) overnight. The next morning, another 30% H ₂ O ₂ (10.8 ml, 0.106 mol, 1.05 equiv.) Was introduced into it at a temperature of 0 ^° C. The reaction mixture was stirred at 0 ^{° C.} for 9 hours, then placed in a refrigerator for the night. An additional 30% H ₂ O ₂ (10.8 ml, 0.106 mol, 1.05 equiv.) Was added at 0 ^{° C.} the next morning. After 3.5 hours, the reaction mixture is poured into 2 l of ice water, thoroughly mixed, then filtered.

Similarly, a mixture of 2-chloro-4-chlorosulphenyl-3-cyano-1- (2 ', 6'-dichloro-4-trifluoromethylphenyl) pyrrole and 2-chloro-3-cyano-4-dichlorofluoromethylsulphenyl-1- (2' , 6'-dichloro-4'-trifluoromethylphenyl) pyrrole (40.77 g, 0.0848 mol, 1.0 equiv.) Is dissolved in trifluoroacetic acid (188 ml) at 0 ^° C. To this is added dropwise 30% H ₂ O ₂ (17.7 ml, 0.173 mol, 2.05 equiv.). The reaction mixture is stirred at 0 ^{° C.} for 2 hours and 45 minutes, then refrigerated (10 ^{° C.} ) overnight. After stirring for 8 hours at 0 ^{° C., the} reaction mixture was again refrigerated overnight. Then the reaction mixture is warmed to room temperature and moves overnight at room temperature. The next morning, another 30% H ₂ O ₂ (9.05 ml, 0.0886 mol, 1.05 equiv.) Is added at 0 ^° C and the reaction is carried out at 0 ^° C for 6 hours 40 minutes, after which the reaction mixture warms to room temperature and mixes from Saturday to Monday. This reaction mixture is poured into 2 liters of ice water, mixed thoroughly, then filtered.

The precipitates formed in both reactions are combined and dissolved in 500 ml of dichloromethane, washed with 500 ml of water, 500 ml of 10% aqueous NaHSO ₃ and 500 ml of NaCl. The organic phase is dried over Na ₂ SO ₄ is filtered and the solvent is evaporated. The result is 74.96 g (yield 79.9%) of a solid. This product was recrystallized from 690 ml of a mixture of hexane dichloromethane (2: 1), to which 20 ml of dichloromethane was added, and the result was 6.98 g of a solid identified as 2-chloro-4-chlorosulfonyl-3-cyano-1 - ( 2'6'-dichloro-4'-trifluoromethylphenyl) pyrrole (Example 22A). Then this product is recrystallized from 103 ml of isopropanol, and the result is 3.97 g of product with a melting point of 187 188.5 ^o C.

2-chloro-4-chlorosulfonyl-3-cyano-1- (2 ', 6'-dichloro-4'-trifluoromethylphenyl) pyrrole (3.97 g, 9.06 mmol, 1.0 equiv.) Was dissolved in tetrahydrofuran ( THF) (15.8 ml) at 0 ^° C. Triphenylphosphine (2.41 g, 1.0 eq.) Is added as a solid. The solution turns yellow. After 2.5 hours, the ice bath was removed and the solution was stirred at room temperature overnight. A further portion of triphenylphosphine (2.55 g, 9.72 mmol, 1.06 eq) was added and the reaction mixture was stirred at room temperature overnight. The formation of sediment. 3 ml of tetrahydrofuran (THF) was added and the reaction mixture was washed twice with saturated NaCl and subjected to back extraction. The organic phase is dried over MgSO ₄ , filtered and the solvent evaporated in vacuo to give a paraffinic solid, 9.44 g. This product is chromatographed on silica gel to give 3.39 g of a paraffinic solid. This product is then recrystallized from 140 ml of isopropanol, and the result is 2.54 g (74.9%) of bis- [2-chloro-3-cyano-1- (2 ', 6'-dichloro-4'-trifluoromethylphenyl) -pyrrol4-yl] disulfide (Example 22B) with a melting point of 218.8 220.3 ^o C.

Bis- [2-chloro-3-cyano-1- (2 ', 6-dichloro-4-trifluoromethylphenyl) pyrrol-4-yl] disulfide (0.80 g, 1.08 mmol, 1.0 equiv.) Is dissolved in dimethylformamide (10 ml) and cooled to O ^o C. Na ₂ HPO ₄ (0.46 g, 3.24 mmol, 3.0 eq.) is dissolved in 5 ml of water, then introduced into a solution of dimethylformamide (DMF). A precipitate forms, to which 15 ml of dimethylformamide and 10 ml of water are added. Solid Na ₂ S ₂ O ₄ (0.564 g, 3.24 mmol, 3.0 eq.) Was added. The reaction mixture turned pale yellow. Dibromodifluoromethane (0.65 g, 3.1 mmol, 2.87 equiv.) Is introduced into the cooled graduated flask, and then transferred to the reaction mixture. This reaction mixture becomes colorless with a white precipitate forming. After 1 hour 50 minutes, 10 ml of dimethylformamide is introduced, after which an additional 0.93 g of CBr ₂ F ₂ is introduced and the reaction vessel is sealed and its contents are stirred at room temperature overnight. After cooling to 0 ^{° C., the} reaction mixture was introduced into 200 ml of water and extracted four times with 150 ml of ethyl ether. The organic phase is washed twice with 100 ml of a 5% aqueous HCl solution, twice with 100 ml of saturated NaHCO ₃ and 100 ml of saturated NaCl. The organic phase is dried over MgSO ₄ , filtered and the solvent evaporated in vacuo. The result is 80.7 mg of a white solid. Then, the initial aqueous phase is filtered to give a white solid that precipitated overnight. This substance is dissolved in dichloromethane, the solvent is evaporated in vacuo, the precipitate is dried and 0.348 g of a white solid is obtained (total yield 0.429 g, 40%). This product combines with 80.7 mg of the sample and is chromatographed on silica gel to give 0.362 g of a white solid, identified as 4-bromodifluoromethylsulphenyl-2-chloro-3-cyano-1- (2 ', 6'-dichloro-4' trifluoromethylphenyl) pyrrole (Example 22C) with a melting point of 128.3 133.7 ^° C.

Additional Synthesis Examples
Following the procedures described in detail above for the synthesis of compounds of Example 1 to 22, or other synthetic methods or procedures described in the general definition of the present invention, a series of pyrrole compounds of formula (I) are prepared according to additional synthesis examples (ASE). The structures of these compounds and the corresponding melting points of these compounds are given in table 3 (ASE N 1-91 compounds of formula (I) in which X ² and X ³ represent hydrogen and the other substituents have the same meanings as defined above), and in table 4 (ASE N 92 195 compounds of formula (1), where X ² and X ³ represent hydrogen, X ¹ and X ⁴ represent chlorine, Y represents trifluoromethyl, and other substituents have the same meanings as previously defined )

Pesticidal Uses and Compositions
The compounds according to the invention are used to control arthropods, especially insects and arachnids, plant nematodes and helminths or the simplest types of pests in the locus (locus) which consists in treating this locus (for example, by introducing or administering the drug) with an effective amount of a compound of the general formula ( I), in which various symbols have the meanings defined above.

In particular, the compounds of general formula (I) are used in the field of veterinary medicine and livestock farming, as well as to protect people from the effects of arthropods, helminths or protozoa, which are internal and external parasites of vertebrates, especially warm-blooded vertebrates, for example humans and domestic animals such as cattle, sheep, goats, horses, poultry, dogs and cats, for example ticks (Acarina), including source ticks (for example, Ixodes spp. boophilus spp. for example, Boophilus microplus , Amblyomma spp. Hyalocuma spp. Rhipioephalus spp. E.g., Rhipicephalus appendiculatus, Halmaphysalis spp. Dermacentor spp. Ormithodorus spp. E.g., Ornithodorus mou bata and ticks, e.g. Datalinia spp. Dermahysssspopabopopopopina gallata Chorioptes spp. Demodex spp. Butrombiculos spp.);
dipterans (e.g. Aedes spp. Anopheles spp. Musu spp. Hypoderma spp. Simulium spp.);
half-winged (bugs) (e.g. Triatoma spp. Phthiraptes e.g. Demalinia spp. Linognathus spp.);
fleas (e.g. Ctenocephalides spp.)
dictiopters (e.g. Blatella spp. Periplaneta spp.);
Hymenoptera (e.g. Monomorium pharaoms);
can be used, for example, to combat the infection of the gastrointestinal tract caused by parasitic nematode worms, for example, worms from the family Trichostrongylidae, Nippostrongylus brasiliensis, Trichinella spiralis, Haemochus contortus, Trihostrongylus colu briformis, Hematodirus battus, Ostertopria trichin circumus, Ostertopria trichinum. and Hymenolepts;
for the elimination and treatment of diseases caused by simple organisms, for example, Eimeria spp. e.g. Eimerria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima and Eimeria necatrix, Trypanosoma cruzi, Leishamania spp. Plasmodium spp. Babessia spp. Trichomonadidal spp. Histomona spp. Giardia spp., Toxoplasma spp. Entamolba hystolytica and Theileria spp.

can be used to protect stored products, such as cereals, including grains and flour, peanuts, animal feed, wood and household property, such as carpets and textiles, from arthropods, especially from beetles, including weevils, moths and ticks, such as Ephestia (mill ognevka), Anthrenus Spp. (museum beetle), Trilolium spp. (Little flour meal), Stophilus spp. (barn weevil) and Acarus spp. (mite), for controlling cockroaches, ants and termites and similar arthropod pests in infected houses and adjacent buildings and sites, and for controlling mosquito larvae in drains and discharge channels, wells, water basins and other sources of standing and running water;
for the treatment of foundations, structures and soil, to prevent exposure of buildings to termites such as Reticulitermes spp. Heterotermes spp. Coptotermes spp.

in agriculture for the destruction of adult individuals, larvae and testicles of Lepidoptera (moths and moths), for example Heliothis spp. such as Heliothis vitescens (Hornworm butterfly), Heliothis armigera and Heliothis zea, Spodoptera spp. such as S.exempta, S. (Egyptian cotton scoop), S. eridania (false scoop). Mamestra configurata (butterfly extension) Barias spp. e.g. E.insulana (boxworm), Pictinophora spp. (e.g. Pectinophora gossypiella, (pink boxworm), Ostrinia spp. e.g. O. nubilalis (corn moth), Trichoplusiani (cabbage worm), Pieris spp. (cabbage caterpillar), Laphugma spp. (scoop marching worm). Agrotis and. . (gnawing scoop), wiseana spp. (butterfly porina), chilo spp. (rice stalk driller), Tropozura spp. and Diatrala spp. (sugarcane mint and rice moth), Sparganothis pilliriana (grape leaflet), Cydia pomella codling moth), Archips spp. (mesh leaflet), Plutella xylostella (cabbage moth),
to combat adults and beetle larvae (beetles), for example Aurothenemus hampli (coffee beetle), Aylesinus spp. (bark beetle), Authonomus grandis (cotton weevil), Acalymma spp. (leaf beetle), Lecuma spp., Psylliodes spp. hertinotarsa decemlinedta (potato flea Colorado potato beetle), Diabrotica spp. (long-louse flea), Gonocephalum spp. (striped false worm), Agrioter spp. (hairy worm), Dermolepida and Aeteronychus spp. (vermiform white larva), phaedon cochlearial (mustard beetle), hissorhoptrus oryzophilus (weevil rice waterweed), meligethes spp. (rice beetle), Centorhynchys spp, Rhynehophorus and Cosmopolites spp. (mowing alfalfa);
for the control of Hemoptera, for example Psylla spp. Bemisia spp. Trialeurodes spp, Aphis spp, Myzus spp, Megoura vicial, Phylloxera spp. Adelges spp, Phorodon humuli (aphid hop), Aeneolamia spp, hephotettix spp. (filly cicadas), Empoasea spp, hilaparvata spp, Perkinsiella spp, Pyrilla spp, Acnidiella spp. (scutellum red) Coccus spp. Pseucoccus spp., Aelopeltis spp. (mosquito bug), hygus spp, Dysdereus spp, Oxycarenus spp, hezara spp,
for controlling Hymenoptera, for example Athalia spp. and Cephus spp. (real sawfly), Atta spp. (leaf ant);
to combat dipterans, for example Aylemyia spp. (root fly), Atheridona spp. and chlorops spp. (spring fly), Phytomyza spp. (beet fly), Geratitis spp. and (common fruit fly);
to combat vesicles, such as Thrips tabaci; with orthoptera such as hocusta and Schistocerca spp. (filly cicadas) and crickets, for example Gryllys spp, and Acheta spp, with claws, for example Smint hurus spp. u Onychiurus spp. (springtail),
to deal with termites, for example Odontotermes spp. (termites), with tick-borne insects, for example Forficula spp. (earwig), as well as other arthropods common in crops such as tick-borne organisms (ticks), for example Tetranyclues spp. Panonychus Bryobia spp. (spider mite), briophyes spp. (halo forming mite), Polyphagotara sonenues spp. Blaniulus spp. (millipedes), Scuttigerella spp. (scolopendrella) Oniseus spp. (Woodlice) u Triops spp. (Crustacean tick);
to combat nematodes that infect plants and trees that are very important for agriculture, affect forest crops and garden plants either by direct infection or by spreading bacterial viruses or that cause mycoplasma or fungal diseases of plants, to combat nematodes that infect the root system such as Meloidogyne spp. (e.g. Mincognita), beet nematodes (e.g. Globodera spp. e.g. G.rostochiensis); Aeterodera spp. (e.g. H.avenae); Radopholus spp. (e.g. R. Similis)
to combat nematodes, such as Pratylenehus spp. (e.g. P.pratensis); Belonolaimus spp. (e.g. B. gracilis); Tylenchulus spp. (e.g. T.semipenetrans); Kotylenchulus spp. (e.g. renifornui); Rotylenchus spp. (e.g. R.robustus); Helicotylenchus spp. (e.g. H.multicinetus); Hemicycliophora spp. (e.g. H. gracilis); Criconemoides spp. (e.g. C. similis); Trichodorus spp. (e.g. T.primitious)
to combat baldness nematodes such as Xiphinema spp. (e.g. X. diversicandatum) hongidorus spp. (e.g. L.elongatus); Hoplolarmus spp. (e.g. H.coronatus); Aphelencheides spp. (e.g. A.ritzema-bosi, A.besseyl),
to combat stem nematodes such as Ditylenchus spp. (e.g. D.dipsaci).

Other harmful insects on which the compounds of this invention can exert include: isopods, for example Oniseus asellus, Armadillidium vulgase and Porcello seaber; from a two-legged family, for example Blaniulus guttulatus; from the family of the leg-bearing, for example, Glophilus carpophagus u Sentigeraspex; from the scolopendrell family, for example, Scutigerella immaculata; from the campodide family, for example hepisma saccharin; from the family of springtails, for example Onychiurus armatua; from the family of orthoptera, for example, Blatta orientalis, Periplaneta americana Leucophaea maderae, Blatella germainica, Acheta dobeatiaus, Gryllotalpa spp. Locusta migrotoria migratorioides, Melanopli diffarentalis Schistocerca gregaris;
from the family of six-winged, for example Forticula auricularia; from a termite family, for example Reticulitermes spp; from a family of lice, for example Phylloxera vastatrix; Pemphgus Pediculurhumanus corporis, Haematopinus spp. Linagnathus spp; from the family of the carnivore (or lice-beetle), for example Trichodectes spp. Damalinea spp; from the family of vesicles, for example, Hercinathrips femoralls Thrips tabaci; from the family of Hemoptera, for example Eurygaster spp. Dysdercus intetmedius, Plesma quadrata, Cimex lectularius, Rhodnius prolixus Triatoma spp.

from the family of beetles, for example, Anobium Punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Adgelastica alru, Leptinotarsa decemlideata, Phaedop cochleariae, Diatroticaphala chppila, ppp. Oryzaephilus surinamnnsis, Anthonomus spp. Sitophilus spp. Ottorrhyqchus sulcatus, Cosmpplites sordidus, Ceuthorrhynehus assimilus, Hypera posti Dermestes spp. Trogoderma spp. Anthrenus spp. Attagenus sp Lyctus spp. Maligethis aeneus, Ptinus spp. Niptus hololeucx Phorodoq humuli, Rhopalospiphum padi, Empoasca spp. Euccelis bilobatus, Nephotetix cineticeps, Lecanium corni, Saisaetia oleae, Laodelphax striatellus, Nilapatvata lugens, Aonidiella aursotii, Aspidiotus hederae, Pseudococcus spp. Psylia spp;
from the lepidopteran family, for example, Pectinophora gossypiella, Bupalus piniariuns, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella muculipennis, Malacosoma neustria, Euproctis chrysorrhoema, Lymantriapp. Bucculatrix thurberiella, Phyllocnistic citrella, Agtotis spp. Euxoa spp. Feltia spp. Earias insulana, Heliothis spp Laphygme exigna, Mamestra brassicae, Panolis flammea, Prodenia Lituta, Spodoptera spp. Txichoplusiani, Carpocaspa pemonella, Pieris spp. Chilo spp. Pyrausta nubilalis, Ephestiakuehniella, Galleria mellonella, Tineola bisselli-ella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capus reticulana, Choristoneura furmiferana Clysia ambiquells, Homona magnanidime. Gibbium psylloides, Tyibolium spp. Tenebrio miolitor, Agriotes spp. Conoderus spp. Melolontha melolontha, Amphimallon soletitialis Coatelytra zealandrica;
from the Hymenoptera family, for example Diprion spp. Hoplocama spp. Lasius spp. Monomorium pharaonis Vespa spp. from a family of dipterans, for example Aedes spp. Anopheles spp. Culex spp. Dxosophila melanogaster, Musca spp. Fannia spp. Calliphora erythrocephala, Lucilia spp. Chxysomya spp. Cuterebra spp. Castrophilus spp. Hyppobosc spp. Stomoxys spp. Oeatrus spp. Hypoderma spp. Tabanus spp. Tannia spp. Bibio hortulanus, Oacinella frit, Phorbia spp. Pegomyia hyoseyant, Gcratitis capitata, Dacus oleal Tipula paludosa;
from a flea family, for example Xenopsylla cheopis Ceratophyllus spp. from the arachnid family, for example Scorpio maurus Latrodectus mactans; from the family of homopterans, e.g. Aleurodes brassica, Bemieia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevioryne brassicae, Crypto myrus ribis, Doralis fabae, Doralis pomi, Eriosoma laniqerum Hyalopterus arundinis, Macrosiphum a

 The present invention provides a method for controlling arthropods and plant pests, which consists in applying to the plants or introducing into the environment where these plants grow, an effective amount of a compound of general formula (I).

 To combat arthropods and nematodes, the active compound is usually introduced into the locus (or locus) where infection with arthropods or nematodes should be prevented, with a dose of about 0.005 to 15 kg of active compound per hectare of the treated area, preferably a dose of 0.02 to 2 kg per hectare. Under ideal conditions, depending on the type of pest that is being controlled, a lower dose may provide the required protection. On the other hand, adverse weather conditions, pest resistance and other factors may be the reason that the active ingredient must be used in higher proportions. When processing foliage, a dose of from 0.01 to 1 kg per 1 ha can be used. The optimal dose usually depends on the type of pest that is being controlled, as well as on the type and age stage of the infected plant, on the row spacing, and also on the method of drug administration.

 When a pest insect arises in the soil, the preparation containing the active compound is evenly distributed over the entire cultivated area in any suitable manner. The introduction of the drug, if desired, can be carried out on the field or in the growth zone of the culture, usually in the immediate vicinity of seeds or plants that must be protected from parasites. The active ingredient can be washed away into the soil by spraying with water over this area, or it can be left until the rain is naturally exposed. When applied or after application, if desired, the preparation can be mechanically distributed in the soil by, for example, plowing or disking. The introduction of the drug can be carried out before, during or after planting (or sowing) plants, but also germination or after germination.

 Compounds of the general formula (I) can be applied to the soil in solid or liquid form mainly for controlling those nematodes that live in this soil, and can also be applied on foliage mainly for controlling those nematodes that infect ground parts of plants (e.g. Aphelenchoidis spp u Ditylenchus spp, which are indicated above).

 The compounds of general formula (I) can be useful for controlling harmful insects that eat parts of plants that are far from the point of application of the preparation, for example, insects that eat leaves, are destroyed by these compounds introduced into the root system. In addition, these compounds can reduce the harmful effects on plants due to the effect of antifading or repellent effect.

 The compounds of general formula (I) are of particular value for the protection of fields, coarse fodder, plantations, greenhouses, garden crops and vines, ornamental plants and garden and forest trees, for example cereals (such as corn, wheat, rice, sorghum), cotton , tobacco, vegetable and garden crops (such as beans, cabbage, lettuce, onions, tomatoes and peppers), field crops (such as potatoes, sugar beets, peanuts, soybeans, seed reps), sugar cane plantations, pasture plants and feed zones (such as maize, sorghum, alfalfa), plantations (such as plantations of tea, coffee, cocoa, bananas, oil palm, coconuts, rubber, spices and spices, fruit nurseries and orchards (for example, planting stone fruits and family fruit trees, citrus trees, kiwi, American avocado, mango, olives and walnuts), vineyards, ornamental plants, flowers and vegetables and shrubs planted in greenhouses, as well as in parks and gardens, forest trees (both deciduous and evergreen) grown in forests, on plantations and nurseries.

 These compounds are of great value for the protection of wood (growing wood, felled wood, treated wood, aged or as building material) from the effects of sawflies (e.g. Mocerus or bugs (e.g., wading beetles, platypuses, wood rodents, bark beetles, lumberjacks, or barrels, grinders), or from the effects of termites, for example Reticulitermes spp, Heterotermes spp, Coptotermes spp.

 They are used to protect stored products, such as grains, fruits, nuts, spices and tobacco, either in a holistic state, or crushed and compounded into products, from exposure to moths, bugs, ticks and weevil-calenderum (Sitophilus granauns) In addition, they serve to protect stored animal products, such as leather, bristles, wool and hides in a natural or processed state, from the effects of moths and bugs, and also protect meat and fish products from bugs, ticks and flies.

 The compounds of general formula (I) can be of particular value in the control of arthropods, helminths or protozoa that damage or spread, or act as carriers of the disease in humans and domestic animals, such as those mentioned above, and they are especially valuable for killing ticks , ticks, lice, fleas, mosquitoes and stinging flies, house flies and infected larvae of flies. The compounds of general formula (I) are especially valuable for killing arthropods, helminths, or protozoa that are present in the body of domestic animals, or that coexist in the skin or suck the blood of an animal. For this purpose, these compounds can be administered orally, parenterally, subcutaneously, or locally to the animal. Coccidiosis, a disease caused by an infectious infection with protozoan parasites of the Eimerita variety, is a serious cause of economic losses caused by a fall in the number of domestic animals and birds, especially where these animals and birds are in areas of severe infection. For example, cattle, sheep, pigs and rabbits can be affected by pests, but the disease is especially severe in poultry, especially in chickens.

 Poultry disease usually spreads from birds swallowing contaminated organisms dispersed in contaminated straw or soil, or when contaminated food or drinking water is consumed. The disease manifests itself in the form of hemorrhage, accumulation of blood clots in the cecum, in the expiration of drops of blood, in weakness and indigestion. Very often, the disease is fatal for the animal, but poultry that have had a severe infection lose significantly in market price as a result of such an infection.

 Administration of a small amount of a compound of general formula (I), preferably in combination with poultry feed, prevents or significantly reduces the possibility of coccidiosis. These compounds are effective both against the intestinal form of the disease (cecum) (caused by E. tenella) and the intestinal form of the disease (mainly caused by E. acervulina, E. brunitti, E. maxima and E.necatrix).

 The compounds of general formula (I) may also have an inhibitory effect on the Oscists due to a significant reduction in the number and / or sporulation of the formed Oscists.

 The compositions described below, intended for local use for people and animals and for the protection of stored products, household goods, property and public places, can also be used to treat useful plant crops and crops growing in the affected area, and can also be used for seed dressing .

The following are the affinities for introducing compounds of general formula (I):
For the treatment of people and animals infected or infected by arthropods, helminths, or protozoa, by parenteral or oral administration or local application of compositions in which the active ingredient produces an instant action and / or has an effect over a long period of time on arthropods, helminths or protozoa, for example by entering them into food or feed, or using swallowed pharmaceuticals, edible seeds, salt licks, feed additives , infused preparations, spraying solutions, dipping solutions, for bath tubs, sprayed solutions, dust preparations, lubricants, shampoos, creams, paraffin lubricants and livestock processing systems, by introducing them into the environment or into special areas where pests can nest including products, timber, household property, industrial and private buildings, for example in the form of spray jets, dusts, smoke, paraffin ointments, varnishes, granular preparations and feed, and in the form of drip feed into waterways, wells , reservoirs and other sources of standing and running water, by introducing into the body of domestic animals in the form of feed for the destruction of larvae of flies feeding on their feces, into cultivated crops in the form of solutions for spraying foliage, dusts, granules, emulsions and foams, as well as in the form of suspensions of finely ground encapsulated compounds of the general formula (I) for soil and root treatment using liquid sprinklers, dusts, granules, smoke and foams; and for seed treatment through liquid sludge and dusts.

 The compounds of general formula (I) can be added to control arthropods, helminths, or protozoa in compositions of any known type suitable for treating vertebrates internally or externally, or to control arthropods in any building, both inside houses and in adjoining areas, and these compositions contain, as an active ingredient, at least one compound of the general formula (I) in combination with one or more compatible diluents or stimulants suitable for the desired wow use. All such compositions can be obtained by known methods.

 Compositions suitable for administration to vertebrates or humans include preparations suitable for oral, transeral, subcutaneous, eg, infusion, or topical administration. Compositions for oral administration include one or more compounds of general formula (I) in combination with pharmaceutically acceptable carriers or coatings, and include, for example, tablets, pills, capsules, pastes, gels, drip formulations, medicinal feed additives, slow release boluses of the preparation, or other means of slow release of the drug, which should remain in the gastrointestinal tract. Any such agents may include the active ingredient contained in the microcapsules, or opened with acid labile or alkaline labile or other pharmaceutically acceptable coatings suitable for intestines. Food premixes and concentrates containing the compounds of this invention may be used for use in the preparation of therapeutic diets, drinking water or other products consumed by animals.

 Compositions for parenteral administration include solutions, emulsions or suspensions in any pharmaceutically acceptable carrier and solid or semi-solid subcutaneous implants, or granules intended to excrete the active ingredient over an extended period, and they must be prepared sterile in any known manner.

 Compositions for subcutaneous administration in topical application include spray solutions, dusts, dipping solutions, bath bath solutions, spray solutions, ointments, shampoos, creams, paraffin lubricants, or infusion preparations and devices. For example, earrings attached to the animal outside in such a way as to ensure local or systemic destruction of arthropods).

 Solid or liquid arthropod suppressants include one or more compounds of the general formula (I) and a din diluent carrier, which may include an edible substance or some other product so as to induce arthropod consumption. When used in agriculture, the compounds of this invention are rarely used alone, they form part of the composition. These compositions, which can be used as insecticides, contain a compound of the invention, such as described above, as an active ingredient, in combination with agriculturally suitable carriers and surfactants that are equally suitable for agriculture . Inert and conventional carriers and conventional surfactants can be used in particular. These compositions form part of this invention.

 These compositions may also contain all types of other ingredients, such as protective colloids, adhesives, thickeners, thixotropic agents, foams, spray oils (especially for acaricidal use), stabilizers, preservatives (especially mold preservatives, sequestrants, etc. as well as other known active ingredients having pesticidal properties (in particular insecticides or fungicides) or ingredients with plant growth regulating properties. according to the present invention, can be in combination with solid or liquid additives commonly used in formulations.

 Doses of the compounds used according to this invention can vary widely depending on the type of insect to be destroyed and the degree of infection of the crops with these harmful insects.

 Typically, compositions of the present invention contain from about 0.05 to about 95 weight. one or more active ingredients corresponding to this invention, from about 1 to 95 weight. one or more solid or liquid carriers, from about 0.2 to 50 weight. one or more surfactants.

 Thus, the compounds of the present invention are usually in combination with carriers and, if desired, with surfactants.

 By "carrier" is meant an organic or inorganic ingredient, natural or synthetic, in combination with which is an active ingredient that serves to facilitate the application of this active ingredient to plants, seeds or soil. In this regard, this carrier is usually inert and should be applicable to agriculture, especially for processing plants. The carrier may be solid (clays, natural or synthetic silicates, silicas, resins, paraffins, solid fertilizers, for example ammonium salts, and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earth and crushed synthetic minerals such as silica, alumina, silicates, especially aluminum or magnesium silicates. Coarse crushed and fractionated rocks, such as calcite, marble, pumice, seriolite and dolomat, as well as synthetic granules of inorganic and organic stone flour, and granules of organic materials such as sawdust, coconut shell, corn cob and tobacco stalks, kieselguhr, grain husks, tricalcium phosphate, powder cork, carbon black adsorbent and water-soluble polymers, resins, paraffins, solid fertilizers, and such solid compositions, if desired, may contain one or more wetting, dispersing, emulsifying or coloring solid agents that can serve as a diluent). The carrier may also be liquid alcohols, especially butanol or glycol, as well as their ethers or esters, especially methyl glycol acetate, ketones, especially acetone, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, and isophorone, petroleum fractions, paraffinic or aromatic hydrocarbons, especially xylene, or alkyl naphthalene petroleum fractions, mineral and vegetable oils, chlorinated aliphatic hydrocarbons, especially trichloroethane or methylene chloride, or aromatic chlorinated hydrocarbons, especially chlorobenzenes, water imye or strongly polar solvents such as dimethylformamide, dimethylsulfoxide or N-methylpyrrolidone as well as water, liquefied gases, etc. and their mixture.

 The surfactant may be an emulsifying agent, a dispersing agent, or a wetting agent. These can be, for example, salts of polyacrylic acids, salts of lignosulfonic acids, sulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (especially alkyl phenols or aryl phenols), salts of esters , taurine derivatives (especially alkyl taurates), esters of phosphoric acid and alcohol or polycondensates of ethylene oxide with phenols, fatty acid esters with polyato GOVERNMENTAL alcohols and sulfate, sulfonate and phosphate derivatives of the above compounds. The presence of at least one surfactant usually plays an important role when the active ingredient and / or inert carrier are only slightly water-soluble or completely insoluble in water and the carrier is water.

 Compositions of this invention may also contain various additives, such as adhesives and dyes.

 Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lactins, and synthetic phospholipids can be used in these compositions. Other additives may be mineral and vegetable oils. Dyes such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metallophthalocyanine dyes, and additional nutrients such as salts of iron, manganese, boron, copper can also be used. , cobalt, molybdenum and zinc.

 Compositions containing compounds of general formula (I) that can be used to kill arthropods, plant nematodes, helminths, or protozoa can also contain synergists (e.g. piperonyl butylate or sesame oil), stabilizing agents, other insecticides, acaricides, plant nematodes, anthelmintic agents and anticoccidioses, fungicides (agricultural or veterinary, for example benomil, iprodon), bactericides, attracting substances or repellents for nistonogih and vertebrate or pheromones reodorenty, flavoring agents, dyes and auxiliary therapeutic agents, eg trace elements. They can serve to increase the potency, durability, safety, consumption, where desired, of the spectrum of exterminated insect pests or to enable other useful functions of this composition to be performed when processing the same animals or the same zones.

 Examples of other pesticidal active compounds that can be included or used in combination with the compositions of this invention are acephate, chlorpyrifos, demotone, methyl, disulfotone, etoprofos, phenytrotion, malathion, monocrotophos, parathion, fosalone, pyrimiphos, methyl, thiazophos , tsiflyutrin, cypermethrin, deltemetrin, fenpropatrin, fenvalerate, permethrin, aldicarb, carbosulfan, meotomil, oxamil, pyrimicarb, bendiocarb, teflubenzuron, dicofol, aerosulfan, lindine, cartan, tsigexatin, tetrademi, tetradi rmectin, milbenmycins, thiophanate, trichlorfon, dichlorose, diaveridine and dimetriadazole.

 For agricultural use, the compounds of formula (I) are usually used in the form of compositions that are in various solid or liquid forms. Liquid compositions can be used to treat substrates or areas that are infected or susceptible to arthropod infection, including structures, indoor buildings and outdoor areas, production sites, containers and equipment and bodies of water with standing or running water.

 Solid homogeneous or heterogeneous compositions containing one or more compounds of the general formula (I), for example granules, tablets, briquettes or capsules, can be used to treat standing or running water for a certain period of time. A similar effect can be achieved by using water-dispersible concentrates, supplied in the form of drops or served with food.

 Compositions in the form of aerosols and aqueous or non-aqueous solutions or dispersions suitable for spraying, droplet irrigation, or weak or ultra-weak spraying can also be used.

 The solid forms of the compositions are dusty powders (containing up to 80% of a compound of formula I) and / or wettable powders or granules, especially those obtained by extrusion, compaction (compression), impregnation of a granular support or granulation using initial powders) (with a content of a compound of formula (I) in these wettable powders or granules ranging from 0.5 to 80%).

 Solutions can be used, in particular emulsion concentrates, emulsions, highly flowing liquids, aerosols, wettable powders (or powders for spraying), dry flowable preparations and pastes as forms of compositions that should be liquid in their practical use.

 Emulsion or soluble concentrates most often contain the active ingredient also in an amount of 5 to 80%, while emulsions or solutions ready for use contain from 0.01 to 20% of the active ingredient. In addition to the solvent, emulsion concentrates may contain, if necessary, from 2 to 50 suitable additives, such as stabilizers, surfactants, penetrating agents, corrosion inhibitors, dyes or adhesives.

 Emulsions of any desired concentration, which are especially suitable for plants, can be obtained from these concentrates by dilution with water.

 Concentrated suspensions that can be used by spraying are prepared in such a way that they provide a stable liquid product that does not precipitate (fine grinding) and usually contains from 10 to 75% of the active ingredient, from 0.5 to 30% of a surfactant , from 0.1 to 10% of thixotropic agents, from O to 30% of suitable additives, such as foam suppressants, corrosion inhibitors, stabilizers, penetrating agents, adhesions and, as a carrier, water and an organic liquid in which ngredient is poorly soluble or insoluble Some organic solids or insoluble Some organic solids or inorganic salts may be dissolved in the carrier to help prevent settling or as antifreezes for water. Wettable powders (or spray powders) are usually prepared in such a way that they contain from 10 to 80% of the active ingredient and usually contain, in addition to a solid carrier, from O to 5% of a wetting agent, from 3 to 10% of a dispersing agent and, if necessary from O to 60% of one or more stabilizers or other additives, such as penetrating agents or anti-caking agents.

 To obtain these wettable powders, the active ingredient or ingredients are thoroughly mixed in a suitable mixer with additionally introduced substances that can be impregnated into a porous filler or crushed using mills or other grinding aggregates. This results in wettable powders that have great advantages in terms of wettability and suspension, they can be suspended in water, resulting in the desired concentration, and this suspension can be used with great success for processing foliage.

 “Water-dispersible boundaries (WG) (granules that are readily dispersible in water) have a composition that is very close to the composition of wettable powders. They can be prepared by granulating the formulations described for wettable powders or by wet methods (contacting the finely divided active ingredient with an inert filler and a small amount of water, for example, from 1 to 20% or with an aqueous solution of a dispersing agent or binder, followed by drying and sieving), or by dry method (compaction followed by and subdivision and screening).

 As already mentioned above, compositions that can be used according to the present invention include aqueous dispersions and emulsions, for example compositions obtained by diluting with water a wettable powder or an emulsion concentrate according to the invention. These emulsions may be of type water in oil or of type oil in water, and they may have a thick consistency.

 All of these aqueous dispersions or emulsions or spray mixtures can be applied to plants by any suitable technique, for example by spraying, in doses usually ranging from 100 to 1200 liters of spray mixture per hectare.

 These products and compositions of the present invention are typically introduced into vegetation, and especially into roots or leaves affected by pests that need to be destroyed.

 Another way to make the compounds or compositions of this invention is to chemitize, that is, to administer compositions containing the active ingredient, irrigation water. This irrigation may be sprinkling for leaf pesticides or may be surface irrigation or underground irrigation for systemic pesticides. The dose of administration of the active ingredient is usually from 0.1 to 10 kg / ha, preferably from 0.5 to 4 kg / ha. These doses and concentrations may vary depending on the method of application and the type of compositions used.

 Typically, compositions for controlling arthropods, plant nematodes, helminths, or protozoa contain from 0.00001 to 95%, especially from 0.0005 to 50% (weight) of one or more compounds of the general formula (I) or the total amount of active ingredients (i.e. compounds of the general formula (I) together with other substances toxic to arthropods and plant nematodes, anthelmintic agents, anticoccidiotic agents, synergists, trace elements or stabilizers). Specifically, the types of compositions used and the doses of their application are selected so that the desired effect (or effects) is achieved by farmers, livestock breeders, doctors and veterinarians, pest control operators, and other specialists. Solid and liquid compositions for local application for use in animals, for the processing of building materials, stored products, household goods, usually contain from 0.00005 to 90%, especially from 0.002 to 10% (weight) of one or more compounds of the general formula (I). Compositions intended for administration to animals orally or parenterally, including subcutaneously, both solid and liquid, usually contain from 0.1 to 80% (weight) of one or more compounds of the general formula (I). Medicated feeds typically contain from 0.001 to 3% (weight) of one or more compounds of the general formula (I). Concentrates and additives for mixing with feeds usually contain from 5 to 90% and preferably from 5 to 50% (weight) of one or more compounds of the general formula (I). Mineral salt licks typically contain from 0.1 to 10% (weight) of one or more compounds of the general formula (I).

 Dusts and liquid compositions for treating livestock, people, goods, buildings and adjacent areas may contain from 0.0001 to 15% and especially from 0.005 to 2.0% (weight) of one or more compounds of the general formula (I). Suitable concentrations are from 0.0001 to 20 ppm, especially from 0.001 to 5.0 ppm of one or more compounds of general formula (I), and they can be used as therapeutic agents in fisheries with suitable exposure times. Edible bait may contain from 0.01 to 5%, preferably from 0.01 to 1.0 weight. one or more compounds of the invention.

 When vertebrates are administered parenterally, orally or subcutaneously or in any other way, the dose of the compounds of general formula (I) will depend on the type, age and health status of the vertebrate and on the type and extent of its actual or potential infection with arthropods, helminths or protozoa pests. Typically, when administered orally or parenterally, the unit dose is from 0.1 to 100 mg, preferably from 2.0 to 20.0 mg per kg of animal body, or it is from 0.01 to 20.0 mg, preferably from 0.1 to 5.0 mg per kg of animal weight per day. When using drugs or slow release devices, the daily doses required for a period of time of a month can be combined and introduced into the body of the animal as a single dose.

 The following examples illustrate agrochemical compositions containing compounds of the invention, as well as insecticidal and acaricidal uses and properties of certain compounds.

Examples of the use of the compositions The following composition examples (examples 23 to 28) illustrate compositions used against arthropods, especially insects and arachnids, plant nematodes and helminths or protozoa, which include compounds of the general formula (I) as active ingredient, especially those described in the examples illustrating the preparation of compounds N 1-22, and in tables 3 and 4. The compositions described in the examples illustrating the compositions, N 23 28, can be diluted with water to obtain individuality sprayable formulations, concentrations suitable for use in the field. General chemical descriptions of the ingredients (for which all percentages indicated are weight percent) used in the compositions of Examples 23-28 are given below.
Ethylene HRV Nonylphenol Ethylene Oxide Condensate
MSU BSU Condensate of tristyrylphenol and ethylene oxide
Arylan CA 70% (w / v) calcium dodecylbenzenesulfonate solution
Solvesso 150 Solvent in the form of a light aromatic hydrocarbon (C 10)
Arylan S Sodium Dodecylbenzenesulfonate
Darval Sodium Lignosulfonate
Celite RF Carrier synthetic magnesium silicate
Sopropol T36 Sodium salt of polycarboxylic acid Rodigel 23 Polysaccharidoxantane resin
Bentolite 38 An organic derivative of magnesium molt morrilolite.

 Aerosil Silicon dioxide with microfine particles.

 Example 23

A water soluble concentrate is prepared from the following ingredients
Active ingredient 7%
Ethyl HRV 10%
N-methylpyrrolidone 83%
by dissolving HRV ethylane in a portion of N-methylpyrrolidone and then adding the active ingredient with heating and stirring to a dissolved state. The resulting solution is brought to the desired volume by introducing the rest of the solvent.

 Example 24

The emulsion concentrate is prepared from the following ingredients
Active ingredient 7%
Sopropol in 4%
Arylan CA 4%
N-methylpyrrolidone 50%
Solvesso 150 35%
by dissolving Sosso BSU, arylane CA and the active ingredient in N-methylpyrrolidone, followed by the addition of Solvesso 150 to the desired volume.

 Example 25

Wettable powder is prepared from the following ingredients:
Active ingredient 40%
Arylan S 2%
Darwan N 2 5%
Celite PF 53%
by mixing the ingredients and grinding the mixture in a hammer mill to obtain a particle size of less than 50 microns.

 Example 26

A water free flowing composition is prepared from the following ingredients:
Active ingredient 40.0%
Ethylene HRV 1.0%
Sopropol TK6 0.20%
Ethylene glycol 5.0%
Rodigel 23 0.15%
Water 53.65%
by thoroughly mixing the ingredients and grinding in a ball mill to obtain an average particle size of less than 3 microns.

PRI me R 27
An emulsion suspension concentrate is prepared from the following ingredients:
Active ingredient 30.0%
Ethylan HRV 10.0%
Bentolite 38 0.5%
Solvesso 150 59.5%
by vigorously mixing the ingredients and grinding them in a ball mill until an average particle size of less than 3 microns is obtained.

 Example 28

Water-dispersible granules are prepared from the following ingredients:
Active ingredient 30%
Darwan N 2 15%
Arylan S 8%
Heals PF 47%
by mixing the ingredients, grinding to a micron particle size in a liquid-energy mill, and then granulating it in a rotary granulator by spraying a sufficient amount of water (up to 10 weight / vol.). The resulting granules are dried in a fluid bed dryer to remove excess water.

 Example 29

Dusty powder can be prepared by vigorously mixing the following ingredients
Active ingredient 1 10%
Ultra Thin Particle Talc 99 99%
This powder can be introduced into the site of infection with arthropods, for example, applied to unloaded garbage or landfill, to stored foods or household items, to animals infected or at risk of infection to destroy arthropods when they swallow the drug. Suitable means for distributing dusty powders in the arthropod infection site are mechanical blowers, hand shakers, and devices for treating animals with a special solution.

 Example 30

Edible bait can be prepared by thoroughly mixing the following ingredients.
Active ingredient 0.1 1.0
Wheat flour 80.0%
Molasses 19.5 19.0
This edible bait can be distributed, for example, in places of residential and industrial buildings and premises, for example in hospitals, in the kitchen, in warehouses, outdoors, in areas infected with arthropods, such as ants, locusts, cockroaches and flies, to destroy these arthropods by swallowing the drug.

 Example 31

A solution may be prepared containing the following ingredients:
Active ingredient 15%
Dimethyl sulfoxide 85%
by dissolving the pyrrole derivative in a portion of dimethyl sulfoxide and then adding an additional portion of dimethyl sulfoxide to the desired volume. This solution can be used to treat domestic animals infected with arthropods by subcutaneous injection in the form of a liquid preparation or after sterilization of the preparation by filtration through a polytetrafluoroethylene membrane (pore size 0.22 μm) by parenteral injection with a dose of 1.2 to 12 ml of solution per 100 kg body weight of the animal.

 Example 32

Wettable powder may be prepared from the following ingredients:
Active ingredient 50%
Ethyl HRV (9 moles of oxide per mole of phenol) 5%
Aerosil 5%
Celite PF 40%
by adsorption of HRV ethylene on aerosil, mixing with other ingredients and grinding in a hammer mill to form a wettable powder that can be diluted with water to a concentration of from 0.001 to 2% (w / v) of the active compound and introduced into the site of infection with arthropods, such as diptera larvae insects or plant nematodes, by spraying or by introducing into the body of animals infected or endangered by arthropods, helminths or protozoa, by spraying sludge and dipping or by oral administration with drinking water to kill arthropods, helminths, or protozoa.

 Example 33

 Slow release pills of the preparation can be prepared from granules containing a sealing filler, a binder, a slow release agent, an active ingredient made according to Example 27 with various percent composition. By compressing the mixture, pills of a density of 2 or more can be obtained that can be introduced into the body of ruminants and can remain in the first part of the stomach of ruminants with slow release of the pyrrole compound for a long period of time to suppress the infection of ruminants caused by arthropods, helminths or protozoa.

 Example 34

The slow release composition may be prepared from the following ingredients:
Active ingredient 0.5 25%
Polyvinyl chloride base 75 99.5%
by mixing the polyvinyl chloride base with the active compound and an appropriate plasticizer, for example dioctyl phthalate, and extruding the melt or pressing in the form of a homogeneous composition to obtain the desired form of the preparation, for example granules, tablets, briquettes or strips for entering into standing water or in the case of alcohols to obtain rings or long earrings attached to ruminants to kill harmful insects by slow release of the active compound.

 Similar compositions can be obtained by replacing the active ingredient in the examples describing the composition with an appropriate amount of any other compound of general formula (I).

Examples of pesticidal methods of using the compositions
In the following Examples 35 to 47 describing the use of the compositions, the compounds of the present invention are used in various concentrations. The use of 1 ppm (the concentration of the compound in the test solution in parts per million) of the solution or suspension or emulsion intended for application to foliage corresponds to approximately 1 g-ha of active ingredient per 1000 l / ha of approximate volume of spray solution ( which is sufficient for sprinkling). Thus, the use of solutions spraying foliage from about 6.25 to 500 ppm will correspond to about 6500 g / ha. When applied to the soil, a concentration of 1 ppm, calculated on the thickness of the soil layer of 7.5 cm, will correspond to approximately 1000 g / ha when processing a sown field.

 Example 35. Effect on aphids.

A mixture is prepared from the following ingredients: 0.01 g of the active ingredient, 0.16 g of dimethylformamide, 0.838 g of acetone, 0.002 g of a mixture of a surfactant, including both an alkylaryl polyester and an alkylaryl polyester whose aryl unit contains sulfo groups; 98.99 g of water
This diluted aqueous mixture is applied by spraying on potted dwarf nasturtium planted with buckthorn aphid (Aphis nosturtii) in stages of larvae and adults. The number of larvae per pot is 100-150. The volume of the spraying water mixture is sufficient to moisten the plants to surface runoff. After spraying, the pots are kept at 20 ^o C for one day, after which the surviving larvae are evaluated. The mortality rate of the larvae was 100% when using the compounds of examples 1,2, 3A, 5, 160, 18, 19 and 20, and ASF N 12, 24, 33, 34, 38, 39, 42, 44, 45, 54, 57, 60, 62, 98 100, 102 104, 125, 128, 130, 135, 137, 141, 142, 144, 157, 158, 162, 166 and 174 at a concentration of 100 ppm.

 Example 36

The procedure was carried out in the same manner as in example 35. However, in this case, 150-200 two-spotted spider mites (Ectranychus urticoe) were bred on the ears of green cabbage. After spraying, the plants were kept at 3 ^° C for five days. The mortality rate of spider mites was 100% for the compounds of examples 2, 3A, 160, 17 and 18 and ASE N 9, 20, 25, 41, 44, 46, 52, 53, 58, 59, 63, 64, 70, 74 , 77 81, 83, 90, 98, 99, 102, 124 and 141 at a concentration of 100 ppm.

 Examples 37 39. Action on the southern scoop.

37. The same recipe is used as in example 35. In this case, the larvae of the southern second age stage scoop larvae (Spodoptera cridonia) are bred on Lima beans with a height of about 15 cm. After five days, the following mortality rate was found. 100% mortality was found when using the compounds of examples 3A, 3B, 5, 6.7, 8.9, 10, 11, 12, 15B, 16C, 17, 18, 20, 21B, 21C and ASE N 42, 44, 60, 62, 64, 98 100, 102, 108, 121, 124, 125, 131, 141, 142, 144, 162, 166 and 174 at a concentration of 10 ^o ppm and 80% mortality was detected using the compound of Example 13 at a concentration of 500 ppm million

38. The same preparation procedure is used as in Example 35, with the difference that the following ingredients are contained in the formulation: 2.5 mg of the active ingredient, 0.05 g of dimethylformamide, 9.9228 g of acetone, 9.0247 g of surface -active substance (as in example 35), 90 g of water
The compound of Example 4 gives a 100% mortality of the southern scoop at a concentration of 25 ppm.

 39. The same preparation procedure is used as in Example 38, with the difference that it contains the following ingredients: 0.625 g of the active ingredient, 12.5 mg of dimethylformamide, 9.9621 g of acetone, 0.0247 g of surfactant ( as in example 35), 90 g of water.

 The compounds of examples 1 and 2 give a 100% mortality of southern scoops at a concentration of 6.25 ppm.

 Examples 40 43. Effect on a Mexican bean seed.

40. The same preparation procedure is used as in Example 37, with the difference that it contains the following ingredients: 12.5 mg of the active ingredient, 0.25 g of dimethylformamide, 9.726 g of acetone, 24.1 mg of surfactant (as in example 35), 89.988 g of water
Mexican legumes (Epilachua varivestie) of the second age stage are bred on lima beans with a height of about 15 cm. Five days later, 100% mortality was detected when exposed to the compound of Example 13 at a concentration of 125 ppm.

 41. Using the same formulation procedure as in Example 38, but containing the compound of Example 8 as the active ingredient, 100% mortality of the Mexican bean at a concentration of 25 ppm is achieved.

 42. Using the same preparation procedure as in Example 35, but containing the compound of Example 15 as an active ingredient, 100% mortality of a Mexican bean seed is obtained at a concentration of 1OO ppm.

 43. The same preparation procedure is used as in Example 40, but in this case it contains the following ingredients: 10 mg of the active ingredient, 0.2 g of dimethylformamide, 9.7657 g of acetone, 0.0243 g of surfactant (as and in example 38), 90 g of water.

 The following mortality rates for Mexican bean kernels are achieved: 80% mortality with the compounds of Example 15A and Example 15B at a concentration of 100 h / min and 100% mortality with the compounds of Examples 1, 2, 9, 17, 18 and ASE n 42, 44, 60, 62, 64, 98, 99, 124, 125, 141, 142 and 144 at a concentration of 100 ppm.

 Examples 44 46. Actions on a home fly.

 A toxic substance in the form of an aqueous sugar solution (10 ml) containing 10% (w / w) sugar and 100 ppm chemical toxic substance is prepared in the same manner as in Example 35. Next, diluted sequential solutions are prepared in accordance with the requirement . Three different formulations are prepared for the test (see table 5).

Twenty-five adult flies (house flies) are anesthetized with carbon dioxide and then transferred by placing them over a cup containing a toxic compound. After exposure for one day at a temperature of 27 ^o With measured the percentage of mortality, which shows the following values:
For example 44: 100% mortality when using the compounds of examples 1, 2, 3B, 4 6, 8, 9, 16C, 17 20, 21B, and 21C and ASE N 42, 44, 60, 62, 64, 98 , 99, 110, 1O2, 103, 121, 124, 125, 131, 141, 142, 144, 162, 166 and 174 at a concentration of 100 ppm.

 For example 45: 100% mortality using the compounds of example 12 at a concentration of 100 ppm.

 For example 46: 100% mortality using the compounds of examples 1, 2 and 5 at a concentration of 12.5 ppm.

 Example 47

 The formulation is prepared in the same manner as in example 35, with the difference that in this case only 48.99 g of water is used, which provides an initial concentration of the test compound of 200 ppm. Aliquots of this formulation are then directly used in accordance with the required concentration (h / min) (parts per million) (weight) according to the following procedure.

 An aliquot of 200 ppm of the test compound (necessary for the final concentration of the test compound), 3.2 ml of water and five seedlings of a grain plant are introduced into a jar containing 60 g of sandy loam loam. The jar is thoroughly shaken to evenly distribute the test formulation in it. After that, twenty testicles of the long-nosed flea beetle are placed in the cavity created in the soil. Vermiculite (1 ml) and water (1.7 ml) are introduced into this cavity. Similarly, a control test is carried out without treatment, using the same volume of an aliquot of an emulsion solution of water - acetone dimethylformamide, without the content of the test compound.

 In addition, a control test with processing is carried out using a commercially available compound prepared in a similar manner that serves as a test standard. Seven days later, live larvae of the long-nosed beetle beetle are counted using the well-known extraction method using a Berles funnel. The compounds of examples 3, 4 and 17-19 and ASE N 98, 99, 101, 105, 113, 119, 121, 124, 125, 130 and 173 provide 100% destruction of the larvae at concentrations of 1.45 ppm, 0.72 ppm and 0.36 ppm Derivatives of pyrroles have moderate toxicity. The toxicity of the pyrroles produced is given in Table 6. TTT1 TTT2 TTT3 TTT4 TTT5 TTT6 TTT7 TTT8 TTT9 TTT10 TTT11 TTT12 TTT13 TTT14 TTT15 TTT16 TTT17 TTT18 TTT19 TTT20 TTT21 TTT22 TTT23 TTT24 TTT25 TTT26 TTT27 TTT28 TTT29 TTT30 TTT31 TTT32 TTT33 TTT34 TTT35 TTT36 TTT37 TTT38 TTT39 TTT40 TTT41 TTT42 TTT43 TTT44 TTT45 TTT46 TTT47 TTT48 TTT49 TTT50

Claims (3)

1. Derivatives of pyrroles of the formula (I)

wherein X is halogen, thiocyanato, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₂ alkylthio halogen containing 3-5 different halogen atoms, halogen C ₁ -C ₂ -alkylsulfonyl containing from 3 to 5 halogen atoms, R'-hydrogen, halogen, amino, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfonyl, trifluoromethylcarbonylamino, C ₁ -C ₄ - alkylthiomethylidenimino, R ² -cyano, formyl, C ₁ -C ₄ -alkyl, difluoromethyl, R ³ -hydrogen, halogen, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, thiocyanato, halo C ₁ -C ₂ -alkylthio containing 3 halogen atoms, a bis (C ₁ -C ₄ -alkyl) m Teal, X ₁ is hydrogen, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkilsulfinil, X ₄ -halo, hydrogen, C ₁ -C ₄ -alkyl, Y- halogen, haloalkyl C ₁ -C ₄ , haloalkoxy-C ₁ -C ₄ , methoxycarbonyl, X ₂ and X ₃ hydrogen; if X ₄ and X _{1 is} hydrogen and X is halogen, then R ₂ has a value other than X.  2. Insectoacaricidal composition comprising a pyrrole derivative and target additives, characterized in that the compound of formula (I) in an amount of 0.05-95 wt. targeted additives rest.  3. A method for controlling insects and ticks by treating them in a distribution center with a pyrrole derivative, characterized in that the treatment is carried out with a compound of formula (I) in an effective amount.

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