Phenylhydrazine derivatives, method of pest control and insecticidenematicides composition

 

(57) Abstract:

The invention relates to compounds having the structural formula I, where X, Y, R and Z are defined in the description of the application. Compounds according to the invention are effective against mites, nematodes, cycatki rice, moths and flea dinosau. Also described methods of obtaining these compounds. The structural formula I

< / BR>
where is a single or double bond. 3 S. and 11 C.p. f-crystals, 8 PL.

The invention relates to new phenylhydrazine derivatives having insecticidal, acaricidal and nematocidal activity.

In addition, the invention relates to insecticidal, acaricidal or nematocidal compositions containing these compounds, and to methods of combating insects, mites and nematodes, by using the above-mentioned compounds or compositions.

The defeat of cultivated plants insects, mites and nematodes is a serious problem for agriculture. Protection from damage by nematodes, mites and insects need many field cultivated plants, such as soybeans, corn, peanuts, cotton, alfalfa, rice, and tobacco.

In addition, the protection against destruction of the criminal code, and so p. , and fruit, nut, ornamental, and seed crops such as Apple trees, peach trees, almond trees, citrus trees and grapes.

Therefore, the development of new effective pesticides, including insecticides, acaricides and nematicides, is currently particularly relevant.

The main research efforts are directed, in particular, on the development of these pesticides, which would have as ovicide and larvicide activity.

Known alkylphenolethoxylate intended for use as acaricides (Chemical Abstracts 108(19): 163280d).

Been disclosed substituted phenylhydrazine and phenyloxazolidine intended for use as pesticides (U.S. patent 4725302).

Famous 7-substituted 2,3-dihydrobenzofuran intended for use as pesticides or chemical intermediates (Europatent 006747). Described arylhydrazines triperoxonane acid with fungicide, bactericide, acaricide and antiseptic activity ("Derwent", abstract 88-312695/44).

Were also described various phenylhydrazine that have activity against insects is th activity (application France 2440943).

The invention relates to a compound having structural formula I

< / BR>
where

simple or double bond;

Y' is hydrogen;

n and m are independently 1 or 0;

A and B is hydrogen or a group of the formula

< / BR>
Y - H, C1-C4-alkanoyl, C1-C4-halogenoalkanes, C1-C4-dialkoxybenzene, C1-C4-alkylaminocarbonyl, halogen-(C1-C4)-alkylsulfonyl, C1-C4-alkoxycarbonyl;

R - H, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkane, halogeno-(C1-C6)alkyl, C1-C6-alkoxy-(C1-C6)-alkyl, phenyl-(C1-C6)-alkoxy, C2-C6alkenyl, C1-C6-alkylthio, C1-C6-alkoxycarbonyl, C1-C6-alkylamino, furyl, thienyl, phenyl-(C1-C6)alkyl, halogeno-(C1-C6)-alkoxy, phenyloxy-C3-C6-cycloalkyl;

Z is O or S, provided that when X is phenyl, R is not alkylamino-band or C1-C6-alkoxycarbonyl; provided that n and m is always equal to 0 when the means of the double bond; provided that when A and B are hydrogen, X means: (a) phenyl, lower funeralcare group, phenoxy group or benzyl, with the phenyl to the for (b) one Deputy from the group (a) - phenyl, and the second is selected from C1-C4-alkoxy, halogen, C1-C4-alkyl and C1-C4-allylthiourea, or when A and B are other than hydrogen, X is hydrogen or lower alkoxy.

The invention relates also to insecticidenematicides compositions containing as active ingredient a compound of General formula I and an acceptable carrier.

The invention also relates to a method of combating pests of cultivated plants, such as insects, mites or nematodes, which is that the places that need protection from defeat these pests treated with an effective amount of the compounds of formula I.

The proposed compounds have the structural formula I, defined above. Preferred are compounds in which Y is hydrogen or COCF3.

The compounds of formula I can be obtained by reaction of the substituted phenylhydrazine

< / BR>
with allermuir agent

< / BR>
where Z is halogen or

< / BR>
and the equivalent of HCl acceptor such as pyridine, in a solvent such as toluene. The product of this reaction can then be allerban or subjected to oxidation using kislay structural formula I; (b) the corresponding carrier. This carrier can be solid or liquid.

Examples of suitable liquid carriers can serve as water, alcohols, ketones, phenols, toluene and xylene. In order to facilitate the transportation and application of the final compositions in the composition may be incorporated various additives which are usually used in such cases, for example one or more surface-active substances (surfactants) and/or inert diluents.

Alternative specified pesticide composition may contain solid carriers and constructed in the form of Farrukh Dustov, granules, wettable powders, pastes, aerosols, emulsions, emulsifiable concentrates and water-soluble solid products.

For example, pesticide compounds according to the invention can be used in the form of Farrukh Dustov, which after mixing with the powdered solid carriers (or absorb on these media, such as mineral silicates, such as mica, talc, pyrophyllite and clays, as well as with surface - active dispersing agent, to form a wettable powder, which may then be directly applied to the target areas.

Alternative powdered solid carrier, stereoinversion directly to the destination.

Granular compositions containing the above compounds and designed to make projections of the row making, introducing into the soil and seed treatment, made preferably using media in a granular or palletirovanie form, such as granular clays, vermiculite, charcoal or rods corn cobs.

Alternative when using liquid media pesticide compounds may be introduced in liquid or solution for spraying, for example in solutions containing joint with this connection solvent, such as acetone, benzene, toluene or kerosene, or these compounds may be dispersed in prestorage environment, for example in water.

For another way of making pesticidal compositions, such as aerosol treatment, the active compound may be dissolved in an aerosol medium, which when increased pressure is fluid, and at atmospheric pressure and normal temperature, for example 20oC is the gas.

The aerosol composition may also be obtained by first dissolving the compound in a less volatile solvent is pesticide processing plant (the term "plant" also includes parts of the plant) of the compounds according to the invention is preferably administered in water emulsion, containing a surface - active dispersing agent, which may be nonionic, cationogenic or anionic.

Suitable surface-active agents are known compounds, such as compounds described in U.S. patent 2547724 (columns 3 and 4).

Compounds according to the invention can be mixed with the abovementioned surface - active dispersing agents in the presence or in the absence of organic solvent, which results can be obtained concentrates, which, after adding water to form an aqueous slurry of the proposed connections to the desired concentration.

In addition, the compounds according to the invention can be used in combination with carriers, which themselves possess pesticidal activity, such as insecticidal, acaricidal, fungicidal or bactericidal activity.

It should be noted that the number of pesticide active compound in the composition will depend on the specific pest, on the particular composition and its composition, method of applying the compounds/compositions and specifically from the treated area, and therefore pesticide effective number of active connections can provide the active ingredient in pesticide-effective compositions may be in the range from about 0.1 to about 95 wt.%.

Breeding for spraying can be only a few parts per million, although, on the other hand, using techniques for ultra-small volumes can be successfully used highly concentrated formulations of the compounds according to the invention.

If parts of the processing are the plants themselves, the concentration per unit area can be from about 0.01 to about 50 pounds per acre, and for such crops as corn, tobacco, rice, and so forth, it is preferable to use a concentration of from about 0.1 to about 10 pounds per acre.

For insect control solutions for spraying compounds can be applied directly to the pests or plants on which they feed or nest. These pesticide active composition can be introduced into the soil or in another environment, which is inhabited by pests.

Harmful insects, nematodes and mites infect a wide variety of plants, including ornamental and agricultural crops, and cause significant damage to these plants by eating their roots and/or leaves, sucking the life juices of the plant, leased compounds may be preferably used to minimize or prevent these injuries, caused by plant pests.

The specific methods used, and the selection and concentration of these compounds is largely dependent on geographic region, climate, terrain, tolerance of plants, etc.

In each case, any technician can easily select the appropriate connection and to determine the concentration of this compound and the method of its introduction by ordinary experimentation.

Especially preferred is the use of the compounds as insecticides, nematicides and acaricides by spraying the leaves and/or tillage.

To more clearly illustrate the invention the following are specific examples, which, however, should not be construed as a limitation of the scope and essence of the invention.

Example 1. Receive (4-methoxy- [1,1'-biphenyl]-3-yl)hydrazine hydrochloride (intermediate chemical compound).

To 25 g of 5-phenyl-0-anisidine was added 250 ml of water and 450 ml of concentrated hydrochloric acid and stirred solution was cooled to 0oC.

Then, maintaining the temperature at 0oC, one drop was added 8.6 g of sodium nitrite in 20 is the target of 113 g of tin chloride in 200 ml of concentrated HCl, cooled to -20oC, after which the mixture is again stirred for 1 h

Then the mixture was subjected to vacuum filtration, and the obtained solid residue was left overnight for drying. This solid residue was dissolved in hot water, was subjected to gravity filtration, and the filtrate was cooled on ice.

The resulting solid crystals were subjected to vacuum filtration and the product was left to dry over night. The result of this procedure was obtained 26 g of hydrochloride (4-methoxy-[1,1'-biphenyl]-3-yl)hydrazine.

Example 2. Obtaining 2-(4-methoxy-1,2-biphenyl-3-yl)hydrazine propanoic acid (compound 18).

To 5 g of the product of example 1 was added 100 ml of water and 40 ml of 10% sodium hydroxide solution. The resulting mixture was stirred for one hour at room temperature. Then the mixture was extracted with ether and the ether extract was dried with sodium sulfate within half an hour.

Then the ether extract was filtered and evaporated under reduced pressure, which was obtained 4.6 g of the intermediate - (4-methoxy-[1,1'-biphenyl]-3-yl)hydrazine.

To 4.6 g of the above intermediate was added 150 ml of toluene and 1.58 g of pyridine, parida.

After adding propionitrile the solution was stirred for one hour at 0oC, and then washed twice with 100 ml of water.

Water fraction was dried and extracted with toluene. Toluene fraction, resulting from the extraction were combined and evaporated under reduced pressure.

The obtained solid was washed with hexane and filtered, resulting in a received 3.4 g of 2-(4-methoxy-[1,1'-biphenyl]-3-yl)propanoic acid hydrazide.

Example 3. Obtaining 2-(4-methoxy-[1,1'-biphenyl]-3-yl)-2-(trifloromethyl)propanoic acid hydrazide (compound 73).

To 2.25 g of the product of example 2 was added 150 ml of methylene chloride. The resulting solution was stirred and cooled to 0oC. Then, to the solution drop by drop) was added 1.75 g of the anhydride triperoxonane acid, the flask was closed and the reaction mixture was stirred over night.

After that, the solvent is evaporated under reduced pressure and obtained solid substance was washed with hexane and was filtered.

The result of this procedure received the final product: 2.7 g of 2-(4-methoxy-[1,1'-biphenyl-3-yl)-2-(trifloromethyl)propanoic acid hydrazide, so pl. 126oC.

Example 4. Receive (4-bromo-[1,14 g of 4-bromo-[1,1'-biphenyl]-3-amine was added 25 ml of water and 50 ml of concentrated hydrochloric acid.

The resulting solution was cooled to 0oC. and Then at a temperature of 0oC, to a solution of one drop of solution was added 1.1 g of sodium nitrite in 6 ml of water. After complete addition, the mixture was stirred at 0oC for one hour.

Then to the reaction mixture solution was added 20 g of tin chloride in 20 ml of concentrated hydrochloric acid, cooled to -20oC, and the mixture is again stirred for one hour.

The precipitate was subjected to vacuum filtration and the obtained solid was left to dry over night. Thus received the final product: (4-bromo-[1,1'-biphenyl] hydrazine hydrochloride, which was used in the subsequent reactions without further purification.

Example 5. Getting carboxylate isopropyl 2-(4-bromo-[1,1'-biphenyl]-3-yl)hydrazine (compound 139)

To the product of example 4 was added 100 ml of 10% aqueous sodium hydroxide solution and the resulting mixture was stirred 30 min at 10oC. Then the mixture was extracted with ether, dried with sodium sulfate for 2 h and evaporated, resulting in a received (4-bromo-[1,1'-biphenyl]-3-yl)hydrazine (3 g).

To 3 g of the above hydrazine was added 100 ml of toluene and 1.5 g of pyridine. Recip is isopropylcarbamate in toluene.

After adding isopropylcarbamate the solution was left to stir over night at room temperature.

Then this solution was washed twice each time with 100 ml of water) was dried with sodium sulfate for 2 h and evaporated under reduced pressure.

The resulting solid precipitate was washed with hexane and recrystallized from toluene, resulting in a received 3 g of isopropyl 2-(4-bromo-[1,1'-biphenyl]-3-yl)hydrazinecarboxamide, so pl. 107-108oC.

Example 6. Getting isopropyl (4-bromo-[1,1'-biphenyl]-3-yl)diazocarbonyl (compound 161)

1.7 g of the product of example 4 was added 100 ml of toluene and 0.4 g of palladium charcoal. The resulting mixture was stirred over night at room temperature and then was filtered and the toluene evaporated under reduced pressure.

The result of this procedure were given 1.5 g of isopropyl carboxylate (4-bromo-[1,1'-biphenyl]-3-yl)diazona as a red oily substance.

Example 7. Getting 2-methoxy-3-dibenzofuranes (intermediate chemical compound).

Under stirring to 10 g of 3-amino-2-methoxybenzophenone was added 100 ml of water and 50 ml of concentrated hydrochloric acid. The received RA is in 15 ml of water, while maintaining the temperature at 0oC. After complete addition, the mixture was stirred for 1 h at 0oC.

To the reaction mixture solution was added 40 g of tin chloride in 50 ml of concentrated hydrochloric acid, cooled to -20oC. Then the mixture was stirred for one hour.

The precipitate was subjected to vacuum filtration and the obtained solid was added to a solution of 70 g of sodium hydroxide in 500 ml of water, cooled in an ice bath.

After that, the mixture was extracted with ether, dried with sodium sulfate for 2 h and evaporated to obtain a solid product. This solid product was washed with hexane and was obtained 7 g of 2-methoxy-3-dibenzofuranes, so pl. 113-115oC.

Example 8. Getting carboxylate isopropyl 2-((2-methoxy-3-dibenzofurans)hydrazine (compound 141).

To 2.3 g of the product of example 7 was added 100 ml of toluene and 1 g of pyridine. The resulting mixture was cooled in an ice bath. Then to the mixture drop by drop) was added 10 ml of 1 M solution of isopropylcarbamate in toluene. After adding the solution was left to stir over night at room temperature.

Then the solution washed twice (each time hisa solid residue was washed with hexane and recrystallized from toluene, as a result, we received 2 g of isopropyl carboxylate 2-2-methoxy-3-dibenzofurans)hydrazine, so pl. 178oC.

Example 9. Getting isopropyl (2-methoxy-3-dibenzofurans)diazocarbonyl (compound 157).

To 1.4 g of the product of example 7 was added 100 ml of toluene and 0.3 g of palladium charcoal. The resulting mixture was stirred over night at room temperature, was filtered, and the toluene evaporated under reduced pressure.

The result of this procedure was obtained 1.2 g of isopropyl carboxylate (2-methoxy-3-dibenzofurans)diazona as a red oily substance.

Connection, systematized in table. 1-6 (NN 1-161), were obtained by means basically the same as those described in the examples above.

If the original materials are not commercially available, they can be synthesized by known methods. Each of the thus obtained compounds was analyzed using NMR spectroscopy.

Example 10. Obtaining compositions.

The examples below relate to the use of the compounds as pesticides.

In all the following examples the mother solutions of compounds is named by adding 90 ml of distilled water and a few drops of ethoxylated sorbitanoleat or similar suitable wetting agent.

This mother solution in appropriate dilutions used in each example. All tests discussed below, which include the processing of compounds according to the invention, accompanied by the control tests (no active connection) that allows for appropriate comparison and to calculate the percentage of the extermination of pests.

Example 11. Tested against adults of acarides and against eggs/larval ticks.

One day before processing to each of the two primary leaves of cowpea (one out of every two plants in a pot) was applied molten tanglefoot (sticky paper) in the configuration of figures 8.

In each such configuration is more close to the stalk circle was designed to test ovicidal/larvicide activity, i.e. against eggs/larval ticks, and the circle, the more distant from the stem, was designed to test acaricides against adult ticks.

The day before treatment groups of adult mites (Tetranychus urticae Koch) was transferred to the "avicennia" mugs and females were allowed to lay eggs until until processing was left for one hour, after which they were removed.

Plant otev.

One day after the treatment groups of approximately 25 adult mites moved in circles for acaricides against adults.

Five days later, these groups were examined for detection of living mites remaining on the leaves. The percentage of destruction of ticks was evaluated based on the number of mites surviving on the control plants.

9 days after treatment ovicide/larvicide mugs were examined for detection of hatched eggs and live immature specimens of mites. The percentage of destruction was evaluated based on the number proklyatyh eggs and immature specimens of mites surviving on the control plants.

If the aim of treatment was eggs, the results meant as avicennia (O), if the treatment was aimed at immature specimens, the results meant as a larvicide (L).

The results of the test compounds on the acaricidal activity against Mature individuals (M1) and against eggs/larvae (M10LV) are presented in table.7.

Example 12. Test red fruit mite.

Apple trees (Orchard), infected red fruit mite (Panonychus ulmi), are sprayed with aqueous solutions, emulsifiable concentrates of individual compounds.

Using joint is CLASS="ptx2">

Example 13. The test nematodes.

The mother liquor 3000 hours/million diluted up to 1000 hours/million Then 500 g of soil in pots infested with eggs Javanese root-knot nematodes (Meloidogyne incognita), 25 ml saturated compounds (the experiment was performed for each connection) with the concentration in the soil 50 PM/million

One day after the treatment in each pot was planted two seedlings of tomatoes. 19 days after planting, the roots of the plants were examined for the presence of growths and the Gauls and was estimated percentage of destruction, on the basis of levels of infection control plants.

The results of the tests on the destruction of nematodes (Ne) are presented in table.8.

Example 14. The test using the sheet processing against cycatki rice.

The mother liquor 3000 hours/million diluted up to 1000 hours/million One pot containing approximately 20 seedlings of rice varieties Mars, treated each composition by spraying using a spray gun.

One day after treatment the plants were covered by a tubular cell and every cell of bore 20 adults of cycatki rice (Sogarodes oryzicola).

Five days after the making of cicadas for each pot was counted the number of surviving cicadas and figured potoczny solution at a concentration of 3000 hours/million 0.2 ml of each compound was pietravalle on the inner surface of each of the 5 cameras with dressing, then left for some time to this solution was spread over the entire surface, and was dried for 2 hours

Then in each cell was injected larvae of Heliothis virescens in the second age. After 14 days for each treatment was determined by the number of surviving larvae and calculated the percentage of destruction, after the adjustment according to the formula of Abbott.

The results of the experiment on the destruction scoops (TB) are presented in table.8.

Example 16. Test to destruction of a flea dinosau.

The mother solution (3000 hours/million) was diluted to 100 million D. 2.5 ml each connection has pietravalle on filter paper (Whatman # 3), located at the bottom of a 100 mm Petri dishes. Two seedling corn was soaked with a solution of 100 hours/million within 1 h, and then transferred to Petri dishes.

After 24 h in each Cup was made 5 of larvae of Diabrotica undecimpunctata in the second age. Five days later recorded the number of live larvae and calculated the percentage of destruction, carrying out correction according to the formula of Abbott (see, J. Economic Entomology, 18, 265 - 267, 1925).

The results are presented in table.8.

1. Fining is - ezavisimo 1 or 0;

A and b is hydrogen or a group of the formula

< / BR>
Y is hydrogen, C1- C4-alkanoyl,1- C4-halogenoalkanes,1- C4-dialkoxybenzene,1- C4-alkylaminocarbonyl, halogeno - C1- C4-alkylsulfonyl, or C1- C4-alkoxycarbonyl;

R - H, C1- C6-alkyl, C1- C6-alkoxy, C3- C6-cycloalkane, halogeno-C1- C6-alkyl, C1- C6-alkoxy WITH1- C6-alkyl, phenyl-C1- C6-alkoxy, C2- C6alkenyl,1- C6-alkylthio,1- C6-alkoxycarbonyl,1- C6-alkylamino, furyl or thienyl, phenyl-C1- C6-alkyl, halogeno-C1- C6-alkoxy, phenyloxy or3- C6-cycloalkyl;

Z is O or S, provided that when X is phenyl R alkylamino or1- C6-alkoxycarbonyl, provided that n and m is always equal to 0 when represents a double bond, provided that when a and b is hydrogen, X is (a) phenyl, lower fenilalanina, fenoxaprop or benzyl, with the phenyl ring of each of the specified substituent may be substituted with halogen, lower alkyl, lower alkoxy is, The1- C4- alkyl and C1- C4-allylthiourea, or when a and b are other than hydrogen, X is hydrogen or lower alkoxy.

2. Connection on p. 1 of the formula I

< / BR>
where X is phenyl;

Y is N or COOCF3;

n = 1;

R - CF3WITH1- C4-alkyl, C1- C4-alkoxy or C3- C6-cycloalkyl,

Z is oxygen.

3. Connection on p. 1, having the General formula II

where X is defined in paragraph 1 and represents (a) phenyl, lower fenilalanina, fenoxaprop or benzyl, with the phenyl ring of each substituent may be substituted with halogen, lower alkyl, lower alkoxygroup, or (b) one Deputy - phenyl, and the second is selected from C1- C4-alkoxy, halogen, C1- C4the alkyl and lower ancilliary;

R is hydrogen, C1- C6-alkyl, C1-C6-alkoxy, C1- C4-halogenoalkane or3- C6-cycloalkyl;

Z is oxygen.

4. Connection on p. 3, in which X is phenyl or alkoxy and R - CF3WITH1- C4-alkyl, C1- C4-alkoxy or C3- C6-cycloalkyl.

5. Connection on p. 1, having the General formula III

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where X is hydrogen or lower dryer is within the General formula IV

< / BR>
where X is hydrogen or lower alkoxygroup;

R has the values specified in paragraph 1;

Z is oxygen or sulfur.

7. Method of pest control by processing areas in need of protection from pests, derivatives of phenylhydrazine, characterized in that as the use of phenylhydrazine compound of formula I under item 1 in an effective amount.

8. The method according to p. 7, characterized in that in places inhabited by insects, is used as a compound of General formula I

< / BR>
where simple or double bond;

Y' is hydrogen;

n and m are independently 1 or 0;

A and b is hydrogen or a group of the formula

< / BR>
Y is hydrogen, C1- C4-alkanoyl,1- C2-halogenoalkanes, di-C1- C4-alkoxyphenyl,1-C4-alkylaminocarbonyl, halogen - C1- C4-alkylsulfonyl;

R is hydrogen, C1- C6-alkyl, C1- C6-alkoxy, C3- C6-cycloalkane, halogen - C1- C4-alkyl, C1- C4-alkoxy WITH1- C4-alkyl, benzyloxy, C2- C4alkenyl,1- C4-alkylthio,1- C4-alkoxycarbonyl, thienyl, benzyl, halogen-C1- C4-alkoxy, C3- C6-cyclol the group or WITH1- C4-alkoxycarbonyl, provided that n and m is always equal to 0 when represents a double bond, R - C1- C4-alkoxy, X is phenyl and C1- C4-alkyl, and hydrogen, provided that when a and b is hydrogen, X represents (a) phenyl, phenoxy, benzyl, phenyl-C1- C4-alkoxy or (b) one Deputy - phenyl and the second is selected from the group:1- C4-alkoxy, halogen, C1- C4-alkylthio,1- C4-alkyl, provided that when a and b are other than hydrogen, X1- C4-alkoxy, R1- C4-alkoxy, n and m = 1.

9. The method according to p. 7, characterized in that in places inhabited by ticks, is used as a compound of General formula I, where a simple or a double bond, Y is hydrogen, n and m independently represents 1 or 0, a and b is hydrogen, Y is hydrogen, C1- C4-alkanoyl,1- C4-halogenoalkanes, di-C1- C4-alkoxyphenyl,1- C4-alkylaminocarbonyl, halogen-C1- C4-alkylsulfonyl, C1- C4-alkoxycarbonyl, R is hydrogen, C1- C6-alkyl, C1- C6-alkoxy, C3- C6-cycloalkane, halogen-C1- C4-alkyl, C1- C4-alkoxy-C1< -alkoxycarbonyl, WITH1- C4-alkylamino, thienyl, furyl, halogen-C1- C4-alkoxy, phenoxy,3- C6-cycloalkyl, Z is oxygen or sulfur, provided that when X is phenyl, R is not C1- C4-alkylamino,1- C4-alkoxycarbonyl, provided that n and m = 0, when represents a double bond, X is phenyl and C1- C4-alkoxy, R1- C4-alkoxy, X represents (a) phenyl or phenyl-C1- C4-alkoxy, phenoxy, benzyl, or (b) phenyl and a second component selected from C1- C4-alkoxy, halogen, C1- C4-alkyl, C1- C4-alkylthio.

10. The method according to p. 7, characterized in that in places where live nematodes, is used as a compound of the formula I, where a simple or a double bond, Y' is hydrogen, n and m independently represents 1 and 0, a and b is hydrogen or a group of the formula

< / BR>
Y is hydrogen, C1-C4-alkanoyl,1- C4-halogenoalkanes, di-C1- C4-alkoxyphenyl,1- C4-alkylaminocarbonyl, halogen-C1- C4-alkylsulfonyl, C1- C4-alkoxycarbonyl, R is hydrogen, C1- C6-alkyl, C1- C6-alkoxy, halogen-C1- C4-alkyl, benzyl - C4-alkoxycarbonyl, benzyl, Z is oxygen, provided that when X is phenyl, R is not C1- C4-alkoxycarbonyl, provided that n and m is always equal to 0 when represents a double bond, and In group

< / BR>
X - C1- C4-alkoxy, R1- C4-alkoxy, provided that when a and b are other than hydrogen, X1- C4-alkoxy, R1- C4-alkoxy, provided that when a and b is hydrogen, X represents (a) phenyl, benzyloxy, phenoxy or (b) phenyl and C1- C4-alkoxy.

11. Insecticidenematicides composition comprising an active component derived phenolicresin and an acceptable carrier, characterized in that as a phenylhydrazine derivative it contains a compound of formula I under item 1 in an effective amount.

12. Acaricidal composition according to p. 11, characterized in that it contains a compound of General formula I, where a simple or a double bond, Y' is hydrogen, n and m independently is 1 or 0, a and b are hydrogen, Y is hydrogen, C1- C4-alkanoyl,1- C4-halogenoalkanes, di-C1- C4-alkoxyphenyl,1- C4-alkylaminocarbonyl, halogen-C1- C4-alkylsulfonyl, C1- C4is laksi, halogen-C1- C4-alkyl, C1- C4-alkoxy-C1- C4-alkyl, benzyloxy, C2- C4alkenyl,1- C4-alkylthio,1- C4-alkoxycarbonyl,1- C4-alkylamino, thienyl, furyl, halogen-C1- C4-alkoxy, phenoxy,3- C6-cycloalkyl, Z is oxygen or sulfur, provided that when X is phenyl, R is not C1- C4-alkylamino,1- C4-alkoxycarbonyl, provided that n and m = 0, when represents a double bond, X is phenyl and C1- C4-alkoxy, R1- C4-alkoxy, X represents (a) phenyl or phenyl (C1- C4)-alkoxy, phenoxy, benzyl, or (b) phenyl and a second component selected from C1- C4-alkoxy, halogen, C1- C4-alkyl, C1- C4-alkylthio.

13. Nematocidal composition on p. 11, characterized in that it contains a compound of General formula I, where a simple or a double bond, Y' is hydrogen, n and m independently are equal to 1 and 0, a and b is hydrogen or a group of the formula

< / BR>
Y is hydrogen, C1- C4-alkanoyl,1- C4-halogenoalkanes, di-C1- C4-alkoxyphenyl,1- C4-alkylaminocarbonyl, halogen-SS1- C6-alkoxy, halogen-C1- C4-alkyl, benzyloxy, C2- C4alkenyl,1- C4-alkylthio, halogen-C1- C4-alkoxy, C1- C4-alkoxycarbonyl, benzyl, Z is oxygen, provided that when X is phenyl, R is not C1- C4-alkoxycarbonyl, provided that n and m is always equal to 0 when represents a double bond, and a group of the formula

< / BR>
X - C1- C4-alkoxy, R1- C4-alkoxy, provided that when a and b are other than hydrogen, X1- C4-alkoxy, R1- C4-alkoxy, provided that when a and b is hydrogen, X represents (a) phenyl, benzyloxy, phenoxy AI (b) phenyl and C1- C4-alkoxy.

14. Insecticidal composition according to p. 11, characterized in that it contains a compound of General formula I, where a simple or a double bond, Y' is hydrogen, n and m independently is 1 or 0, a and b is hydrogen or a group of the formula

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Y is hydrogen, C1- C4-alkanoyl,1- C4-halogenoalkanes, di-C1- C4-alkoxyphenyl,1- C4-alkylaminocarbonyl, halogen - C1- C4-alkylsulfonyl, R is hydrogen, C1- C6-alkyl, C1- C6-alkoxy, SUB>4
-alkyl, benzyloxy, C2- C4alkenyl,1- C4-alkylthio,1- C4-alkoxycarbonyl, thienyl, benzyl, halogen-C1- C4-alkoxy, C3- C6-cycloalkyl, Z is oxygen, provided that when X is phenyl, R is not C1- C4-alkylaminocarbonyl or1- C4-alkoxycarbonyl, provided that n and m is always equal to 0 when represents a double bond, R - C1- C4-alkoxy, X is phenyl and C1- C4-alkyl, a and b is hydrogen; provided that when a and b is hydrogen, X represents (a) phenyl, phenoxy, benzyl, phenyl-C1- C4-alkoxy or (b) one Deputy - phenyl and the second is selected from the group:1- C4-alkoxy, halogen, C1- C4-alkylthio,1- C4-alkyl, provided that when a and b are other than hydrogen, X1- C4-alkoxy, R1- C4- alkoxy, n and m = 1.

Priorities signs:

12.11.91 connection of the formula I, where X is phenyl or funeralcare;

20.11.92 - X is different from phenyl, funeralcare.

 

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