JPH0859474A - Treating liquid for preventing bacterial infection of animal - Google Patents

Abstract

PURPOSE: To provide a safe liquid agent effective for preventing the bacterial infection of animals and keeping the effect over a long period of time. CONSTITUTION: This treating liquid is composed of a solution or an emulsion produced by dissolving or dispersing an alkoxysilane compound containing biguanidyl group and expressed by (C2 H5 )3 Si(CH2 )3 NHC(=NH)NH-C(=NH)NH- Z<2> (Z<2> is phenyl which may be substituted with a halogen or trifluoromethyl group) or a guanidylcontaining polysiloxane compound having (CH2 )3 NHC(= NH)NH-C(=NH)NHZ<2> group bonded to at least one Si atom at the chain terminal or in the chain in water and/or an alcohol. The treating liquid has high safety, enables the direct treatment of the surface of animal body and is effective for the sterilization of livestock barns. Treatment of a pregnant pig with the liquid before delivery is effective for preventing the born piglet from diarrhea and skin infection during lactation. Mastitis of dairy cattle can be prevented at least for one month by treating the udder of the dairy cattle with the liquid.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a treatment solution for preventing bacterial infection in animals. The treatment liquid for preventing bacterial infection of animals according to the present invention has a long-lasting effect, and for example, it can prevent bacterial infection in lactating piglets by being used only once in sows before calving, and A single treatment can also prevent mastitis in dairy cows for a long period of time.

[0002]

2. Description of the Related Art Piglets for feeding meat during lactation from birth to weaning are prone to develop bacterial infections such as diarrhea and skin diseases due to bacterial infection from sows, which is a major cause of decreased productivity of pigs. There is. Currently, as a measure against this, drugs for piglets
Methods (eg, antibiotics) are administered orally, or sterilization is performed by spraying a bactericide on the pigs and the entire stalls.

However, oral administration of a drug poses a safety problem because of the risk of the drug remaining in meat.
Further, spraying of a bactericide has a low effect persistence, and even if spraying is frequently performed, a sufficient bactericidal effect may not be obtained.

Also in dairy cows, a method of immersing the udder in a liquid medicine has been used to prevent mastitis due to bacterial infection of the udder. However, in this case also, the bactericidal effect is not long-lasting and the treatment is frequently performed. Had to do.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a treatment solution for preventing bacterial infection in animals, which has a very high bactericidal effect after spraying.

[0006]

The present inventors have previously dissolved or dispersed in a water and / or alcohol a hydrolyzable silane compound and a polysiloxane compound containing a guanidyl group such as a biguanidyl group or a cyanoguanidyl group. Solutions or emulsions are various materials
It has been found to be useful as a bactericidal agent (eg, cloth, glass). In subsequent research, this silane compound containing guanidyl group and polysiloxane compound were also effective for sterilization of livestock and livestock, and the sterilization effect lasted for a very long time,
For example, it has been found that a single spraying on a pre-partum sow can provide an excellent effect of preventing diarrhea and skin diseases during lactation of a piglet born from the sow.

The present invention is represented by a solution of a guanidyl group-containing silane compound represented by the following general formula (1) or an acid addition salt thereof in water and / or alcohol, or by the following general formula (2). A treatment solution for preventing bacterial infection for animals, which comprises a solution or emulsion containing a polysiloxane compound having a guanidyl group-containing siloxane moiety or an acid addition salt thereof in water and / or alcohol.

X ¹ X ² X ³ Si-Y-NHC (= NH) NH-Z ¹ (1)

[0009]

Embedded image

In the formula, at least one of X ^{1 to} X ³ is a hydrolyzable group, the rest is a hydrocarbon group, X ⁴ is a C _{1 to} C ₅ alkyl group, and Y is a C _{1 to} C ₂₀ alkylene. Is a group, Z ¹ is —CN or —C (═NH) NH—Z ² , where Z ² is H, a C ₁ -C ₂₀ alkyl group, or a substituted or unsubstituted phenyl group.

The -NHC (= NH) NH-Z ¹ group is a cyanoguanidyl group [-NHC (= NH) NH-CN] when Z ¹ is a -CN group.
And when Z ¹ is a -C (= NH) NH-Z ² group, it is a biguanidyl group [-NHC (= NH) NH-C (= NH) NH-Z ² ].

In the general formula (1), the hydrolyzable group represented by X ^{1 to} X ³ is preferably an alkoxy group such as a methoxy group or an ethoxy group, or a halogen such as chlorine. On the other hand, X ¹ ~
The hydrocarbon group for X ³ is preferably a C ₁ -C ₅ alkyl group such as methyl or ethyl, an alicyclic group such as cyclohexyl, or an aromatic group such as phenyl. Preferably 2 of X ^{1 to} X ³
One or more is a hydrolyzable group, particularly preferably X ^{1 to} X ³
Are all hydrolyzable groups.

C _{1 to} C of Y in the general formulas (1) and (2)
Examples of ₂₀ alkylene groups include methylene, ethylene, propylene, hexylene, octylene, decylene, eicosylene and the like. Preferably, Y is a C ₂ -C ₁₀ alkylene group. When Z ¹ is a group represented by -NHC (= NH) NH-Z ²
(That is, when the silane compound has a biguanidyl group), Z ² is hydrogen, C _{1 to} C ₂₀ alkyl group (eg, methyl, ethyl, propyl, hexyl, decyl, eicosyl, etc.)
, Or a phenyl group, and the phenyl group may be substituted with a halogen such as fluorine, chlorine or bromine, or a trifluoromethyl group.

In both the general formula (1) and the general formula (2), Y is a propylene group and Z ¹ is -C (= NH) NH-Z ²
A compound in which Z ² is a substituted phenyl group having a substituent such as a halogen or a trifluoromethyl group is preferable from the viewpoints of both ease of synthesis (availability of raw materials) and antibacterial activity.

A guanidyl group-containing silane compound represented by the general formula (1) and a method for producing the same are described in JP-A-5-247066. That is, a corresponding silane compound having an amino group, represented by the general formula X ¹ X ² X ³ Si-Y-NH ₂ , is reacted with NC-N = C (SCH ₃ ) NH ₂ or NaN (CN) _2. And let
The amino group is cyanoguanidylated to obtain a cyanoguanidyl group-containing silane compound in which Z ¹ is —CN in the general formula (1). When this cyanoguanidyl group-containing silane compound is reacted with an amine represented by the general formula Z ² -NH ₂ , Z ¹ is a -C (= NH) NH-Z ² group in the general formula (1). A silane compound is obtained. These silane compounds, both in their free base and acid addition salt form, are soluble in water and alcohol. Therefore, either form can be used. The acid addition salt may be any of inorganic acid salts such as hydrochloride and nitrate, and organic acid salts such as acetate, tartrate, citrate, lactate and gluconate.

Specific examples of the silane compound represented by the general formula (1) are shown below. (C ₂ H ₅ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-CN (CH ₃ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-CN (C ₂ H ₅ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-C (= NH) NH-Z ² (CH ₃ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-C (= NH) NH-Z ² Where Z ² = phenyl, p-chlorophenyl, p-fluorophenyl, p-trifluoromethylphenyl, or 2,4-
Dichlorophenyl.

A polysiloxane compound having a guanidyl group-containing siloxane moiety represented by the general formula (2) and a method for producing the same are described in Japanese Patent Application No. 3-359590. When the corresponding amino group-containing polysiloxane compound is cyanoguanidylated in the same reaction as above, Z ¹ in the general formula (2)
A cyanoguanidyl group-containing polysiloxane compound in which is --CN 3 and is further reacted with an amine,
A biguanidyl group-containing polysiloxane compound in which Z ¹ is a —C (═NH) NH—Z ² group in the general formula (2) is obtained.

The polysiloxane compound used in the present invention is
It suffices to have at least one guanidyl group-containing siloxane moiety represented by the general formula (2) thus formed in the molecule. The bonding position of the guanidyl group-containing siloxane moiety may be either at the end of the molecule composed of the polysiloxane chain or within the chain. For example, the guanidyl group-containing siloxane moiety represented by the general formula (2) may be bonded to one or both ends of the molecule and / or may be present at one or more positions in the chain. The structure of the other siloxane moiety of the polysiloxane molecule is not particularly limited and may be the same as the ordinary polysiloxane compound known as silicone. For example, as with dimethyl polysiloxane which is a representative example of silicone, although other siloxane moiety may consist dimethylsiloxane -Si (CH _{3) 2} -O- chain, it may be other dialkyl siloxane moiety, also The alkyl group portion may have a functional group (eg, amino group). Further, the other siloxane moiety may have two or more kinds of repeating units.

An example of the guanidyl group-containing polysiloxane compound used in the present invention is represented by the following general formula (3).

[0020]

[Chemical 3]

In the formula, A is an amino group, a cyanoguanidyl group [-NHC (= NH) NH-CN], or a biguanidyl group [-NHC (=
NH) NH-C (= NH) NH-Z ² ]. n is 1 to 10, m is 4 to 200
Within the range of. Preferably, A contains at least 50% or more biguanidyl groups, n is 3 (ie, Y is propylene), and the m value is about 10 to 50 (eg, about 20) on average. The fact that A contains 50% of biguanidyl groups means that the biguanidyl groups are bonded to only one of the molecular ends on average.

The properties of the guanidyl group-containing polysiloxane compound are the same as those of silicone, and change from oily to rubbery to solid resin depending on the molecular weight. In the present invention, those having a molecular weight range that is soluble or emulsifiable in water or alcohol are used. A preferred polysiloxane compound is
It is an oily substance having a viscosity at 25 ° C of 0.1 to 1 million cSt, particularly 5 to 50,000 cSt. This polysiloxane compound can also be used in the form of either a free base or an acid addition salt.

The treatment solution for preventing bacterial infections for animals of the present invention is produced by dissolving or emulsifying at least one of the above-mentioned guanidyl group-containing silane compound and polysiloxane compound in a solvent selected from water and alcohol. It In the case of a silane compound, since it is dissolved in a solvent, it is used as a solution. When the polysiloxane compound does not dissolve in the solvent, it is emulsified in the solvent and used as an emulsion. It is also possible to use two or more kinds of any one of the silane compound and the polysiloxane compound, or to use the silane compound and the polysiloxane compound together.

The solvent may be water or alcohol alone, or a mixed solvent of water / alcohol. As the alcohol, ethanol and isopropanol are preferably used in consideration of toxicity. The concentration of the silane compound or the polysiloxane compound in the treatment liquid is not particularly limited and is usually 0.02 to 10 although it varies depending on the application and the compound used.
It is preferably within the range of 0.2 to 5% by weight, particularly 0.2 to 5% by weight. This treatment liquid contains the above-mentioned silane compound and / or the active ingredient.
Alternatively, in addition to the polysiloxane compound, a small amount of additives such as an emulsion stabilizer (in the case of emulsion) may be contained.

The treatment liquid for preventing bacterial infections for animals of the present invention can be used by an appropriate method such as spraying, coating, dipping or the like on the body surface of livestock or a livestock barn. Thereby, a siloxane polymer or polysiloxane film containing an antibacterial guanidyl group is formed on the surface of the object to be treated. Specifically, in the case of a silane compound, it is hydrolyzed by a solvent or water in the air to produce a polymer having a siloxane bond (Si-O) as a skeleton (siloxane polymer) as a hydrolysis product, Form a film. In the case of a polysiloxane compound, the film is formed as it is. The siloxane polymer or polysiloxane film has durability because it is bonded to the surface of the object to be treated, and the effect continues even if it is washed with water or rubbed. However, since the amount of adhesion is very small on the body surface, direct treatment of the body surface of an animal does not impede respiration or other adverse health effects. The silane compound and polysiloxane used in the present invention are
Both are of the same type as those called silicones, which are often inert and harmless to animals (including humans), as can be seen, for example, from their use in implants in the human body. Are known. As shown in the examples, the treatment liquid of the present invention shows no toxicity even when used directly on the body surface of animals.

The treatment liquid of the present invention is prepared, for example, by treating the whole body of a sow before delivery with a method such as spraying or coating.
It is possible to prevent bacterial infections (diarrhea, skin diseases, etc.) during lactation in piglets born from the sows. In other words, since the bactericidal effect is highly durable, it is possible to prevent neonatal piglets with weak resistance from bacterial infection by treating the mother pig only once (without treating shock-sensitive piglets). Excellent effect can be obtained. In this case, it is appropriate that the amount of the treatment liquid used is about 20 to 500 mL per sow.

The treatment liquid of the present invention is also effective in preventing mastitis in dairy cows. In this case, it is convenient to immerse the udder of the dairy cow in the solution of the treatment liquid periodically (eg, once every 1 to 2 months), but other treatment methods (application, spraying)
Is also possible.

Furthermore, the treatment liquid of the present invention can be used for disinfecting livestock houses. In this case, the barn can be effectively disinfected, for example, by spraying or applying once every 1-2 months. The amount of treatment liquid used in this case is 5 to 50 per 1 m ^2.
About mL is appropriate. Of course, it is also effective for sterilizing and disinfecting animals other than livestock such as pets and animal sheds, and thereby it is possible to exert a preventive effect against bacterial infections under various situations. For example, the generation of offensive odor can be prevented by spraying pets such as dogs and cats.

[0029]

【Example】

[0030]

Example 1 Preparation of a treatment liquid consisting of a 1% by weight aqueous solution of a cyanoguanidyl group-containing silane compound represented by a structural formula of (C ₂ H ₅ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-CN did. This processing liquid
100 mL was sprayed on the whole body of 20 mother pigs 3 days before calving, and the piglets born from this mother pig were weaned after calving (after birth).
The clinical symptoms (presence or absence of diarrhea and skin diseases) and developmental status of bacterial infections were observed up to 25 days. Table 1 shows the observation results
Shown in

[0031]

Example 2 (C ₂ H ₅ O) ₃ Si (CH ₂ ) ₃ NHC (= NH) NH-C (= NH) NH-Z ²
The same test as in Example 1 was conducted using a treatment liquid consisting of a 1 wt% aqueous solution of a biguanidyl group-containing silane compound (hydrochloride) represented by HCl (in the formula, Z ² = p-chlorophenyl). The results are also shown in Table 1.

[0032]

Example 3 A polysiloxane compound represented by the above general formula (3) (wherein, m = average 20, n = 3, 50% is a biguanidyl group and the remaining 50% is an amino group) (that is, average) Prepared by dispersing a hydrochloride of a polysiloxane compound having a biguanidyl group bonded to one end of the molecule in water to prepare 1% by weight
The same test as in Example 1 was conducted using the aqueous solution as the treatment liquid. The results are also shown in Table 1.

[0033]

Comparative Example 1 A piglet born from 20 mother pigs that had not been treated before delivery was observed in the same manner as in Example 1. The results are also shown in Table 1.

Each item in Table 1 is obtained as follows.

-Diarrhea incidence (%) = total number of diarrhea occurrence during lactation period / (number of lactation x lactation day age) x 100-Skin disease incidence (%) = = total skin disease occurrence during lactation period Number of cows / (number of lactating animals x day of lactation) x 100 ・ Nursing rate (%) = number of weaning animals / number of lactation starting animals x 100 (In addition to diarrhea, piglets have many debilitating deaths of unknown cause.)

[0036]

[Table 1]

As can be seen from Table 1, the bacterial infection (diarrhea, skin disease) of lactating piglets can be significantly reduced by treating the sows before calving only once with the treatment liquid of the present invention. It was possible and the preventive effect was remarkable. In addition, especially as a result of preventing diarrhea, the mortality rate during lactation decreased (lactation rate increased)
And, during that time, my weight gain also increased. Comparing the effects of the examples, a particularly high effect was obtained in the treatment liquids containing the silane compound having a biguanidyl group and the polysiloxane compound as active ingredients (Examples 2 and 3), but the compound having a cyanoguanidyl group was used as an active ingredient. The treatment liquid (Example 1) also has a remarkable bactericidal effect as compared with the comparative example. In addition, in Examples 1 to 3, no adverse effects due to the treatment were observed in the breeding observation results for the mother pig sprayed with the treatment liquid of the present invention.

[0038]

Example 4 Treatment of the present invention comprising a 1 wt% solution of the biguanidyl group-containing silane compound (hydrochloride) used in Example 2 in a water / ethanol mixed solvent (30/70 by weight). The liquid was used to dip the whole udder of 20 dairy cows, and the development of mastitis was observed for one month thereafter. Table 2 shows the results.

[0039]

[Comparative Example 2] The occurrence of mastitis for 20 months in the same period and in the same stall as in Example 4 for 20 cows treated with only the above mixed solvent without treatment with the treatment liquid according to the present invention Was observed. Table 2 shows the results.

[0040]

[Table 2]

With respect to mastitis of dairy cows, a single treatment with the treatment liquid of the present invention showed a continuous bactericidal effect capable of preventing mastitis for at least one month.

[0042]

INDUSTRIAL APPLICABILITY The treatment solution for preventing bacterial infection of animals of the present invention comprises
It is highly safe and can directly treat the animal's body surface by spraying, applying, dipping, etc., and has a long-lasting effect, and a single treatment can exert a bactericidal effect for a long period of time. As a result, for example, a single treatment of pre-partum sows can prevent newborn piglets from being infected with bacterial infections (diarrhea, skin disorders, etc.) throughout the lactation period and also contribute to weight gain during weaning. A significant increase is observed. Death and developmental failure due to bacterial infection of newborn piglets are major problems in pig farming, and this can be prevented by a simple operation of spraying the treatment liquid of the present invention once on a sow before delivery. It is expected to make a great contribution to improving pig productivity.

The treatment liquid of the present invention can prevent mastitis for at least one month after treating the udder of a dairy cow once. Therefore, the required number of treatments is significantly reduced as compared with the conventional sterilizing chemical liquid, which usually requires treatment each time milking.

As can be seen from the above, the treatment liquid for preventing bacterial infections for animals of the present invention has the safety of being able to directly treat the surface of the animal body, and exhibits a high bactericidal effect over a long period of time by a single treatment. Besides the above, it is useful for all purposes of sterilization across animals and barns.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display area C08G 77/388 NUJ // C07F 7/10 W 7/18 P C08G 77/26 NUJ

Claims (2)

[Claims] 1. A treatment solution for preventing bacterial infections for animals, which comprises a solution of a guanidyl group-containing silane compound represented by the following general formula (1) or an acid addition salt thereof in water and / or alcohol. X ¹ X ² X ³ Si-Y-NHC (= NH) NH-Z ¹ (1) In the formula, at least one of X ^{1 to} X ³ is a hydrolyzable group, the rest is a hydrocarbon group, and Y is A C ₁ -C ₂₀ alkylene group,
Z ¹ is -CN or -C (= NH) NH-Z ² , where Z ² is H,
A C ₁ -C ₂₀ alkyl group or a substituted or unsubstituted phenyl group. 2. Prevention of bacterial infections for animals, which comprises a solution or emulsion containing a polysiloxane compound having a guanidyl group-containing siloxane moiety represented by the following general formula (2) or an acid addition salt thereof in water and / or alcohol. Processing liquid. Embedded image In the formula, X ⁴ is a C ₁ -C ₅ alkyl group, Y is a C ₁ -C ₂₀ alkylene group, Z ¹ is -CN or -C (= NH) NH-Z ² , and Z ² is H, a C ₁ -C ₂₀ alkyl group or a substituted or unsubstituted phenyl group.