RU2113790C1 - Agent for cockroach baiting - Google Patents

Abstract

FIELD: insecticides. SUBSTANCE: agent has an active component and useful carrier if necessary. Agent has at least one compound of the general formula (I)

where R¹ - unsubstituted lower alkyl or substituted with hydroxyl; R² - lower alkyl; m - whole number from 10 to 20 taken at an effective dose and used as an active component. EFFECT: enhanced effectiveness of agent, improved method of synthesis. 2 tbl

Description

 The invention relates to the fight against cockroaches, and more particularly to a tool for bait cockroaches.

 A cockroach bait agent is known that contains sex pheromones of an American cockroach (Periplaneta americana) as an effective amount of a substance (see Bell 1986, Pesticide Control N. 12). A disadvantage of the known agent is that its specificity and activity do not always lead to satisfactory results.

 The objective of the invention is to provide a tool that provides a more effective bait of cockroaches in the process of dealing with them.

,
где R¹ - низший алкил, незамещенный или замещенный гидроксилом;
R² - низший алкил;
m - целое число от 10 до 20
в эффективном количестве.This problem is solved by the proposed means for bait cockroaches, containing the active substance and, if necessary, a suitable carrier, due to the fact that as a substance it contains at least one compound of the general formula

,
where R ¹ is lower alkyl, unsubstituted or substituted by hydroxyl;
R ² is lower alkyl;
m is an integer from 10 to 20
in an effective amount.

Compounds of general formula (I) in which R ¹ and R ^{2 are} lower alkyl and m is an integer from 10 to 20 are widely known (see, for example, An.Bromatol. 30, p. 267 (1979); insect Biochem. 13, p. 381 (1983); J.Chem.Ecol. 6, p. 309 (1980); An. Bromatol. 31, p. 137 (1979); Biochem.Syst.Ecol.16, p. 647 (1988); Riv. Ital. Sostanze Grasse 63, p. 213 (1986); J. Chem. Ecol. 15, p. 939 (1989)) and can be obtained by known methods (see, for example, Org.Reactions 4, p. 378 (1948); Chem. Rev. 65, p. 63, 1965).

,
где R² и m имеют вышеуказанное значение, а W означает низший алкил,
подвергают взаимодействию с восстанавливающим агентом в среде разбавителя.Compounds of general formula (I) in which R ¹ is lower alkyl substituted with hydroxyl, R ² is lower alkyl and m is an integer from 10 to 20, are new. They can be obtained, for example, due to the fact that the ketone of the general formula

,
where R ² and m have the above meaning, and W means lower alkyl,
subjected to interaction with a reducing agent in a diluent medium.

.If 3-methyl-heptadecan-2-one is used as the starting compound, the reaction proceeds according to the following formula of formulas:

.

 The ketones of general formula (II) used as starting material are known or can be prepared by known methods (see Agr. Biol. Chem. 40, p. 391 (1976); J. Org. Chem. 40, p. 3456 (1975); J. Org. Chem. 40, p. 2410 (1975)).

 As the diluent, polar solvents are preferably used, such as, for example, ethanol, propanol, dioxane, dimethyl sulfoxide, dimethylformamide and mixtures thereof. Lower alkanols, such as ethanol and propanol, are particularly preferred.

 Suitable reducing agents are, for example, lithium borohydride, sodium borohydride and lithium alanate, as well as hydrogen in the presence of a conventional hydrogenation catalyst, such as, for example, platinum dioxide or Raney nickel. Sodium borohydride is particularly preferred.

The reaction temperature can vary widely. They preferably operate at temperatures between -20 ^o C and +80 ^o C, in particular at temperatures between 0 and 40 ^o C.

To carry out reduction per mole of the starting compound (II), preferably 1 to 3 mol, in particular 1 mol of a reducing agent, is preferably used. The reactants are preferably fed to the reactor at a temperature of about 0 ^° C. and the reaction mixture is stirred at a slightly elevated temperature until the end of the conversion.

 Processing can be carried out by known methods, for example, due to the fact that the reaction mixture is concentrated, the residue is taken up in water and cyclohexane, extracted with cyclohexane, concentrated again and the resulting crude product is purified by column chromatography.

 The proposed tool can be used in the framework of mechanical methods for controlling cockroaches, for example, in traps or adhesive means, biological or chemical methods for controlling cockroaches, or combined methods for controlling cockroaches. When using mechanical means, the proposed tool can be applied to them over the entire surface, in part or in suitable discrete places, for example, by spreading, spraying, impregnating, printing, if necessary together with other active substances, such as, for example, luring coloring. In the case of the use of biological or chemical methods of controlling cockroaches, the proposed tool can be mixed with pathogenic organisms, such as, for example, viruses or microorganisms, or natural or synthetic insecticides, or it must be in sufficient proximity to these organisms or substances. The above is also valid when using the combined method.

 The proposed tool is preferably included in the bait containing insecticides or in glue traps, or is placed near the bait, for example, above it. The proposed agent may also be in the form of a sustained release preparation in which the compounds of general formula (I) are enclosed or microencapsulated in a polymeric material, paraffins, waxes, and the like. materials. Standard devices can be used as a trap, and as a bait, they are a regular substance for cockroaches. The proposed tool is preferably used in amounts of 0.0001 to 20 mg of the active substance, in particular 0.01 to 0.1 mg, on a bait or trap, for example, an adhesive trap.

The proposed tool can also be used in the form of a standard preparation for spraying, if necessary, in a mixture with suitable insecticides. In this case, all standard preparations are possible, including microcapsules, which can be sprayed with standard devices. It is also possible to use the proposed agent in the form of granular or dust capable of spreading, which may contain suitable insecticides. Moreover, the consumption of the proposed product is preferably 1 to 500 mg of active substance per m ² , in particular 2 to 200 mg of active substance per m ² .

 As insecticides, all substances that are active against cockroaches can be used, since there is no undesirable interaction between insecticides and compounds of the general formula (I).

 In general, the proposed agent may be in the form of preparations standard for insecticidal agents, such as, for example, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic substances impregnated with the active substance, and polymer microcapsules.

 These preparations, which may also contain an insecticide used to control cockroaches, are prepared by known methods, for example, by mixing the active substances with excipients and / or excipients, i.e., liquid solvents and / or solid carriers, if necessary, using surface- active substances, i.e. emulsifiers and / or dispersants and / or foaming agents. In addition, the preparations may also contain conventional adhesion improvers, natural or synthetic phospholipids, mineral or vegetable oils, colorants and trace elements.

 If the preparations are intended as bait, for example, bait for spreading or placed in a specific place, the bait may additionally contain further additives that serve to bait cockroaches and / or to ensure that cockroaches desire to receive insecticides. These additives can be, for example, natural or synthetic flavors, colorants and / or substances that are readily accepted by cockroaches, such as, for example, cereal-based starch and / or sugar products.

 The preparations preferably contain 0.001 to 95 wt.%, In particular 0.01 to 70 wt.%, Of compounds of formula (I).

 The following examples illustrate the preparation of new compounds of formula (I).

 Example 1

,
2 г (7,46 ммоль) 3-метил-гептадекан-2-она растворяют в 20 мл этанола и раствор смешивают с 0,28 (7,46 моль) боргидрида натрия при температуре 0^oC. Дополнительно размешивают при температуре 0^oC в течение двух часов и затем при комнатной температуре в течение двух часов. Реакционную смесь сгущают под пониженным давлением, остаток подают в смесь циклогексана с водой и водную фазу три раза экстрагируют циклогексаном. В результате сушки и сгущения получают 2 г (99% теории) 3-метил-гептадекан-2-ола в качестве чистого вещества.

,
2 g (7.46 mmol) of 3-methyl-heptadecan-2-one is dissolved in 20 ml of ethanol and the solution is mixed with 0.28 (7.46 mol) of sodium borohydride at a temperature of 0 ^o C. Additionally stirred at a temperature of 0 ^o C for two hours and then at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, the residue was taken up in a mixture of cyclohexane and water, and the aqueous phase was extracted three times with cyclohexane. As a result of drying and thickening, 2 g (99% of theory) of 3-methyl-heptadecan-2-ol are obtained as a pure substance.

¹ H-NMR (200 MHz CDCl ₃ ): δ = 0.9 (2d, 6H), 1.18 (t, 3H), 1.2-1.6 (m, 27H), 3.65 (m, 1H).

.The following compounds are prepared analogously:

.

¹ H-NMR (200 MHz, CDCl ₃ ): δ = 0.88 (d + t, 6H), 1.15 (t, 3H), 1.20-1.40 (m, 35H), 3.60 -3.75 (m, 1H).

 Example 2

2 г (7,46 ммоль) 3-метил-гептадекан-2-она в 10 мл диэтиленгликоля смешивают с 1,11 г (22,4 ммоль) гидразингидрата и 1,2 г (29,85 ммоль) гидроокиси натрия. Реакционную смесь перемешивают при температуре 200^oC в течение 20 ч. После охлаждения до комнатной температуры добавляют 100 мл воды, при охлаждении подкисляют соляной кислотой и три раза экстрагируют циклогексаном. Объединенные органические экстракты два раза промывают водой, сушат над сульфатом натрия и сгущают. В результате очистки колоночной хроматографией с применением в качестве растворителя циклогексана получают 1,0 г (53% теории) 3-метилгептадекана.

2 g (7.46 mmol) of 3-methyl-heptadecan-2-one in 10 ml of diethylene glycol are mixed with 1.11 g (22.4 mmol) of hydrazine hydrate and 1.2 g (29.85 mmol) of sodium hydroxide. The reaction mixture was stirred at 200 ^° C. for 20 hours. After cooling to room temperature, 100 ml of water was added, acidified with hydrochloric acid and cooled three times with cyclohexane. The combined organic extracts are washed twice with water, dried over sodium sulfate and concentrated. Purification by column chromatography using cyclohexane as a solvent gives 1.0 g (53% of theory) of 3-methylheptadecane.

MC m / z (%): 254 (23, M ⁺ ), 225 (46), 196 (18), 155 (17), 113 (22), 99 (28), 85 (67), 71 (83) , 57 (100).

¹H-ЯМР (200 Мгц, CCl₃): δ = 0,85 (т, 9H), 1,1-1,4(м, 37H).The following compound is likewise obtained:

¹ H-NMR (200 MHz, CCl ₃ ): δ = 0.85 (t, 9H), 1.1-1.4 (m, 37H).

 The following examples confirm the activity of the proposed tool.

 Example 3. In a room measuring 2.25 x 4.70 m are located in one sheltered place and one watering hole, which are located in two opposite corners, as well as one piece of cracker in the other corners. One day after the release of 20 male cockroaches and 20 female cockroaches (Blattella germanica) at a distance of 40 cm from the rusk, one jar containing the insecticide (in this case, 0.5% of the commercial product ethyl chlorpyrifos) and a tablet feed are placed . On the inner side of the lid of the jar there is a plate which, one hour before the start of the experiment, was treated with a compound of formula (I) dissolved in n-hexane, or only with n-hexane (as a control experiment). Treated jars and untreated jars, respectively, are placed in three rooms of the above size. The next day, determine the mortality of animals. The results of the experiment are summarized in table 1.

Example 4. Ceramic tiles are sprayed with an aqueous solution containing (a) a preparation comprising 50 g / l cyfluthrin insecticide, and (b) said preparation and optionally compound No.3. Cyfluthrin insecticide consumption is 20 mg / m ² tiles, and compound consumption is No. 3-4 mg / m ² tiles. One tile thus treated is placed in the corner of a container measuring 49 x 50 cm and a height of 29.5 cm, in which there is a watering place, feed, a sheltered place, as well as 5 cockroaches — males and cockroaches — of Blattella germanica females, filed in 2 hours before the start of the experiment. Each experiment is repeated three times. After one, two and three days, the mortality of the animals is determined and the average value from three experiments is determined. The results of the experiment are summarized in table 2.

Claims (1)

A cockroach bait agent containing an active substance and, if necessary, a suitable carrier, characterized in that it contains at least one compound of the general formula as an active substance

where R ¹ is lower alkyl, unsubstituted or substituted by hydroxyl;
R ² is lower alkyl;
m is an integer from 10 to 20,
in an effective amount.

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