Insecticide-acaricide substance for against ectoparasites in dogs and cats

FIELD: organic chemistry.

SUBSTANCE: invention describes insecticide-acaricide substance used against extoparasites in dogs and cats. Substance represents derivative of phenylpyrazole of the formula (I) wherein in pyrazole structure cyano-group, trifluoromethylsulfenyl group and amino-group are bound at 3, 4 and 5 positions, respectively, and chlorine atoms are bound to phenyl cycle at 2 and 6 positions, and trichlorosilyl group is bound at 4 position. Substance protects dogs and cats against infection with fleas for 65 days after treatment and for 45 days after treatment of cats, and against infection with mites for 35 days, not less. In acute experiment toxicity of substance is characterized by value LD50 above 1300 mg/kg after its administration in stomach to dogs.

EFFECT: valuable properties of substance.

2 ex

 

This invention relates to the field of veterinary medicine, in particular to the active substances (substances) to combat ectoparasites of dogs and cats.

The proposed substance, representing the derived phenylpyrazole and having a high insecticidal and acaricidal activity at a moderate toxicity to warm-blooded animals, intended for use as an active ingredient of medicines aimed at the destruction of fleas and ticks in dogs and fleas in cats, and also the prevention of infection of the small domestic animals by these parasites.

Known substances of medicinal products intended for combating ectoparasites on cats and dogs, representing a derivative of Imidacloprid; synthetic PYRETHROID is permethrin; organophosphorus substance fenthion (IVAN maple, I.N. Ilyukhin, L.A. Napisana. Reference Foreign veterinary drugs in Russia, 1999-2000, M.: Evers, 1999, p.121; 128; 131-132), as well as substance the same purpose, representing neinogennye surfactants (U.S. Pat. Russia №2034466); permethrin in combination with sulfosalicylate of higher fatty acids (U.S. Pat. Russia №2030869); ethoxylated alkyl phenols (U.S. Pat. Russia №2132613). These substances have only insecticidal action and do not possess acaricidal properties.

Known effective ACAR is cydnie substance. These include, in particular, include organophosphorus substance diazinon (see Reference Vidal, "a Medicinal product for veterinary use in Russia", 2003/2004, M.: Estrofem Service, strb-170); amitraz (U.S. Pat. EPO No. 050535); amitraz in combination with dimethylsulfoxide (U.S. Pat. Russia №2108780); amitraz in combination with prednisolone (see above Reference Vidal, strb-66).

Of course, what is of more practical importance are substances having a combined insecticide and acaricide action. Among such substances include toxic to warm-blooded animals 2-isopropoxyphenyl-N-methylcarbamate (see above reference Irakleiou and others, p.122-124). The best are (as on the effectiveness and safety of use) insectoacaricidic natural origin: aversectin and selamectin (see above Reference Vidal, strb-27 and B-245). A significant drawback of the last two insectoacaricidal is the possibility of side effects and a rapid loss of efficacy after application to the hair of animals.

Currently, the most effective insecticide and acaricide substance is one of the derivatives of phenylpyrazole received international name fipronil and accept us as a prototype of our proposed insecticide and acaricide substance.

Fipronil along with som is Kimi dozens of derivative phenylpyrazole protected by patents of Russia No. 2026291; 2035452; 2051909; 2080789; 2087470; 2106183; 2160535. It should be noted that all other derivatives phenylpyrazole (except fipronil), protected by the mentioned patents, given purely speculative, without substantial justification.

Fipronil is a derivative of phenylpyrazole, which in the structure of pyrazole in the third position attached cyano, fourth - triftormetilfullerenov group, the fifth - amino group, while the phenyl structure in the second and sixth positions of attached chlorine atoms and in the fourth position - triptorelin group. Chemical name of fipronil in rational system: 5 - amino-1-(2,6-dichloro-4-triptoreline)-4-trifloromethyl-3-canoperate.

The structural formula

Fipronil as an insecticide and acaricide substance in the composition of medicines to combat ectoparasites of dogs and cats provides 100%protection dogs from fleas for 2-3 months; from tick - over 1 month and cats from fleas for 40 days after treatment (see attached copy of the prospectus of the company Merial).

However, fipronil has a serious disadvantage in that it has a very high toxicity when injected into the stomach of warm-blooded animals. In particular, the value of LD50upon receipt of fipronil in the RCU rats does not exceed 100 mg/kg, for dogs this size is 640 mg/kg It creates a hazard to persons working with fipronil, and can be dangerous for animals treated with medicines on the basis of fipronil, for example, in case of accidental ingestion or licking wool after processing of these funds.

This invention aims to eliminate this disadvantage by using to combat ectoparasites of dogs and cats insecticide and acaricide substance representing the derived phenylpyrazole, in which (as fipronil), in the structure of pyrazole in the third, fourth and fifth positions are attached respectively cyano, triftormetilfullerenov group and amino group, and a phenyl structure (as fipronil) contains in the 2 and 6 positions of attached chlorine atoms, but in the fourth position (unlike fipronil) instead triptorelin group attached trichlorethylene group. Chemical name proposed insecticide and acaricide substance (rational): 5-amino-(2,6-dichloro-4-trichlorosilane)trifloromethyl-3-canoperate.

The following is the structural formula of the proposed insecticide and acaricide substance

The technical result of the proposals is a significant reduction in the toxic is ti insecticide and acaricide substance with respect to warm-blooded animals compared with the toxicity of the substance of the prototype (fipronil).

In particular, we found that the toxicity of the proposed substance in the acute experience when entering the stomach of rats is characterized by a value LD50in excess of 800 mg/kg, and for dogs greater than 1300 mg/kg

For substance-prototype values found LD50in rats and dogs, respectively 100 and 580 mg/kg (literature data, these values are 100 and 640 mg/kg).

Description Toxicological experiment described in example 1.

Reduction of toxicity insecticide and acaricide substance does not cause deterioration of the entomological activity compared to the entomological activity of the substance of the prototype.

In particular, in the entomological tests it was found that after treatment of dogs with solutions containing the same amount of the proposed substance and the substance of the prototype, the protection of dogs from becoming infected fleas persists 65 days after treatment. For cats duration of protective action from fleas is 45 days. The term of protection from ticks for dogs up to 35 days after treatment with solutions containing equal amounts proposed insecticide and acaricide substance or substance of the prototype.

Description entomological tests presented in example 2.

The proposed insecticide and acaricide substance (5-amino-(2,6-dichloro-trichlorosilane)trifloromethyl-3-cyanopyridine) obtained in the laboratory through targeted chetyrehjadernogo synthesis using reagents produced on an industrial scale.

In the first stage of the synthesis in solution of potassium hydroxide in absolute ethanol was carried out the reaction between acetylcarnitine, ethylcyanoacrylate and Performa. The resulting potassium salt of ethyl-2,3-dicyanodiamide neutralized with hydrochloric acid, receiving the first intermediate - ethyl-2,3-dicyanodiamide, which was isolated from the reaction mixture and passed to the second stage in the form of a solution in a mixture of water and acetic acid.

In the second stage atomistically sodium was added to concentrated sulfuric acid, obtaining a suspension nitrogylcerin acid. This suspension was injected into a solution of 2,6-dichloro-4-trichloroaniline in glacial acetic acid. To the obtained reaction mixture was added with the first stage a solution of ethyl-2,3-dicyanodiamide in a mixture of water - acetic acid.

In the response received from the second intermediate - 5-amino-3-cyano-1-(2,6-dichloro-4-trichlorosilane)pyrazole. This intermediate was isolated from the reaction mixture, was dissolved in dichloromethane and passed to the third stage.

At the third stage to the second solution of the intermediate in dichloromethane solution was added triftormetilfullerenov in dichloromethane. In the reaction carried out at this stage, received the third intermediate - 5-amino-3-cyano-1-(2,6-dichloro-4-trichloro listener)cryptomaterial.

This intermediate was transferred to the fourth (last) stage, where he was treated chloroperbenzoic acid, getting the final product: 5-amino-(2,6-dichloro-4-trichlorosilane)trifloromethyl-3-cyanopyridine.

This product was isolated from the reaction mixture, washed with dichloromethane and dried at 40°C.

Samples of the proposed insecticide and acaricide substance used for chemical identification, definitions of key physico-chemical constants, as well as for Toxicological research and entomological tests.

The structure of the proposed insecticide and acaricide substance was determined by the strategy of purposeful synthesis, however, for its unambiguous identification methods were used x-ray analysis and electron paramagnetic resonance (EPR). Was unequivocally identified by the following structural formula

According to the data obtained by HPLC, the substance obtained by the above method contains about 1.5% related impurities.

The following are the basic physico-chemical constants of the proposed insecticide and acaricide substance:

Appearance: crystalline powder

(GF XI, B.1, s-176)
Solubility, wt.%
in methanol - about 14,0
in ethanol is approximately 6.0
acetone is about 1.0
in the water is less than 0.3
Melting point216-221°
(GF XI, q.1 p.16)
The specific absorbance (A)A=170-173
in the UV spectral region
the maximum absorption
(λ=279 nm). Solution
in methanol, the layer thickness of 1 cm
(GF XI, B.1, p.34-37)

Below in the examples described Toxicological research and entomological tests proposed substance.

Example 1. Toxicological studies.

Toxicological studies suggested insecticide and acaricide substance and parallel insecticide and acaricide substance-prototype (fipronil) were performed using a substance obtained by the method described above, commercial and industrial design of fipronil (manufactured by Rhone Poulenc).

Toxicity studies in acute experience were performed with the standard method, first rats and then on dogs.

Acute toxicity the ri introduction into the stomach of rats.

For the experiment were formed three groups of clinically healthy rats, kept in vivarium conditions. The first and the second group consisted of 24 males and 24 females, the third (control) - 6 males and 6 females.

In the first and second groups animals were divided into subgroups, rats, each of which received different amounts of the investigated material.

The first group received the proposed insecticide and acaricide substance, second - fipronil. The proposed substance and fipronil was administered to animals in the form of a suspension in sunflower oil. Animals of control group received pure sunflower oil. The dose of the substance in 1 and 2 groups varied.

The result of the experiment it was found that for the proposed insecticide and acaricide substance value LD50exceeds 800 mg/kg, the magnitude of the acute toxicity of fipronil was characterized by the value LD50=100 mg/kg, which coincided with the literature data.

Acute toxicity when injected into the stomach of dogs.

In the experiment were taken 38 mongrel dogs of both sexes, divided into two groups, each of which was divided into 4 subgroups. The substance was injected into the stomach of animals in the form of capsules with food. Doses of fipronil was 80; 100; 320 and 760 mg/kg; doses of substance of the proposed structure 200; 400; 1000 and 1600 mg/kg

The experiment established that d is I dogs, treated with fipronil, the value of LD50is 580 mg/kg, which is close to the value published in the literature (640 mg/kg). For insecticide and acaricide substance of the proposed composition of the magnitude of LD50was 1300 mg/kg

Example 2. Entomological tests.

Comparative entomological tests proposed insecticide and acaricide substance and substance-prototype (fipronil).

For entomological tests were used industrial commercial sample of fipronil and sample insecticide and acaricide substance of the proposed composition obtained by the method described above.

Prior to testing, were formed two groups of mongrel dogs aged 4 to 8 years of age weighing from 8 to 14 kg of both sexes. Each group consisted of 20 animals.

For testing on cats were also selected two groups of animals of both sexes 15 goals each. The body weight of the animals ranged from 4 to 12 kg

Dogs and cats were mostly long-haired.

One group of dogs was treated with a solution containing fipronil. The second group of dogs, the solution containing the substance of the proposed structure. Were similarly treated both groups of cats.

The solutions were prepared by dissolving the proposed substance in one case and fipronil in another. In is the quality of the solvent used isopropanol. The concentration of each of the substances was 0.25 g 100 cm3the solvent. In addition to the substances in both solution was injected into the film-forming Kollidon VA-64 (produced by BASF) in an amount of 2 g / 100 cm3the solvent.

Dogs and cats have sprayed prepared solutions from vials, equipped with valves nozzles. The dose solution was for dogs 6 cm3/kg body weight for cats 4 cm3/kg of body weight.

Treated animals throughout the summer season was in areas with pockets of hatching fleas and ticks.

During the test recorded the time from processing to detect parasites on animals.

As a result of tests it is established that the treatment solution containing fipronil, and a solution containing the substance of the proposed structure, provides protection from infection fleas dogs for 65 days of processing and cats - for 45 days. From infected dogs ticks both substance also protects equally - 35 days after processing.

The results of the experiments described in examples 1 and 2, demonstrate that the proposed insecticide and acaricide substance is characterized by a significantly lower toxicity to warm-blooded animals than the substance of the prototype, and not inferior to the latter in entomological efficiency the efficiency.

Insecticide and acaricide substance for combating ectoparasites of dogs and cats, representing the derived phenylpyrazole, which has the structure of pyrazole attached in the third, fourth and fifth positions, respectively, cyano, triftormetilfullerenov group and amino group, and the phenyl cycle attached in the second and sixth positions on the chlorine atom, wherein in the fourth position to the phenyl cycle attached group trichlorosilyl with the following structural formula:



 

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