DE2140862A1 - Preparations for repelling animals, in particular birds and mice - Google Patents

Description

The Upjon Company Kalamazoo, Mich., V.St.A.

Means for repelling animals, in particular birds and

Mice.

The present invention relates to new means for repelling animals, in particular seeds and Plants and plant products for feeding and driving animals out of their areas. The new Agents can be applied as a coating to grains. In this way, damage can be more ready for harvest Prevent plants and freshly planted seeds, especially by birds and mice.

The η £ - or CO -amino- QC, oi- diphenylalkanoamides used as active ingredients for defense against animals are known compounds. In the form of the free base, they have the general form

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. ^E l

E ₂

in which R-, and R ^> independently of one another, hydrogen atoms or alkyl groups with 1 "to k carbon atoms, η the integer 2 or 3» R * and R, independently of one another, alkyl groups with 1 to if carbon atoms or alkenyl groups with 3 or k are carbon atoms and R ^ and R, together with the connected -N ^ atom, form a saturated heterocyclic amino group with 5 to 7 ring atoms and not more than 10 carbon atoms in total.

The quaternary acid addition salts obtainable from the free basic compounds of the formula I Ammonium salts, N-oxides (including acid addition salts of N-oxides) are active and valuable for defense against Animals using a specific active compound or a mixture of two or more active compounds can be formulated and used.

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The numerous and diverse animals that live side by side in many habitats on this earth exist, suggest a law of nature in combat and survival. Man became one in this struggle dominant factor and strives more and more to satisfy the relationships between the various animals to change his own desires. One of the main human needs is nutrition, and that Animals compete with humans for the food produced on earth. The animals are also in the Competition with people and space, and sometimes they go against human aesthetic values. Birds gather at suitable brood nesting places and populate the airspace around the airfields; Rodents undermine the foundations of buildings, gnaw holes in wood, cloth, and paper, and birds like rodents are carriers of pathogenic microorganisms, sometimes threaten human health.

Humans try to modify the fight because of their dominant position. He is constantly increasing the part of the earth in his possession and excluding animals from it to a greater or lesser extent. Competing animals were removed from the human environment by killing them. "Slightly more tolerant procedures for this exclusion have been to deter the animals and put up protective barriers. Today man invents subtle chemical protective barriers through which animals are repelled and a competitive situation is avoided. The present invention is based on the discovery of the defensive effect of Y - or U-) -

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Amino-06, ο6 -diphenylalkanoamides towards animals

The compounds identified as free bases in the above general formula I arouse disgust in animals. The animals seem to abhor the taste of the compounds, although also a disgust. sake against the smell can play a role. This' reluctance was initially in birds, then also in rodents, particularly mice and rats, but especially observed in mice.

According to the present invention, any of the pure compounds of the class under consideration, a mixture of two or more compounds or formulations of the same together with other materials on objects or an area can be applied so that the animals are repelled. These various forms are referred to as an "active agent" of the invention. Birds avoid food that contains an inventive. Agent is coated or impregnated, and they can be of be driven away from sleeping or nesting places. Rodents are also used, for example, by food, fabrics and repel paper coated or impregnated with an active agent and avoid places that are treated with an active agent.

For example, wild mice were given a choice of food containing ^ - (2-methyl-l-pyrrolidinyl) - <X, oC diphenylbutyramide was treated, and not treated in this way

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deltes food was offered, rejected by the treated food when the concentration of compound ^{2 was} 5, 0.5 and 0.1%. The degree of rejection was significant at each concentration according to probability analyzes. When wild mice were offered treated food on the basis of no choice (food intake or starvation), the 2.5 percent concentration was significantly repellent.

The compositions according to the invention can accordingly be mixed with vegetable food sources such as seeds, grain plants, other plants in horticulture and agriculture, applied to these or incorporated into them, so that the mice are repelled so that they, like other high-calorie foods, from damage Can be preserved by rodents “High-calorie food ¹¹ is to be understood as meaning an energy-generating food that is sought and used by animals, in particular birds, mouse and saddle pests. Packaging materials can also be protected from damage by rodents.

It has been found that birds respond particularly to the repulsive effect of the y - or CJ -amino- Oi , cc - diphenylalkanoamides according to the invention. In a field trial, three batches of sweet corn seeds were planted. A lot was not treated with an active agent. The second batch was treated so that it contained 0.5 % (of the seed weight)> f - (2-methyl-1-pyrrolidinyl) - o (, oc diphenylbutyramide. The third batch was 3.0 wt. % of the compound treated The active agent was used in the form of 99.5% dust.

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These batches of treated and untreated sugar corn seeds were planted on 1.2 hectares of plots on both sides of a swamp area known as a breeding and habitat for blackbirds, separated by fields of the same size. 2.1+ randomly selected subunits of around 200 seeds each were found within the 1.2 hectare | Field area observed for bird damage. The threads in each subunit were observed daily from the time of planting to when the corn plants were about 10 cm tall.

The blackbirds destroyed 3,341 seeds and seed plants in the untreated plots, but were lost in the treated only 109 seeds and 95 seed plants damaged. The percentage losses were about 53 and 2%. Within five days of planting, the treated plots were essentially free of noxious blackbirds. In contrast, their activity on the untreated plots was up at least 10 days after loading) Planting strong and lasting.

The effectiveness of the Y or OJ -amino- οί, oC-diphenylalkanoamides used according to the invention as agents with repellent effect on birds is also determined by determining the concentrations which are required in a feed in order to reduce the feed intake by 50 % . When using y- (2-methyl-l-pyrrolidinyl) -o £, oil -diphenylbutyramide, these _{R 5} _ values, expressed in percent by weight, are as follows:

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Quiscalus quiscula 0.056

Passer domesticus 0.261

Agelais phoeniceus 0.091

• Phasianus Suchicus 0.178

Lophortyx californicus "0.178

Coturnix coturnix japonica 0.180

Other compounds of the formula I give the same values with some variations. For example, the Kj-Q value for} f- (2-methylpiperidino) - C \ , οζ. -diphenylbutyramide 0.056 % (Agelaius phoeniceus). Further, particularly active compounds of the formula I are:

"Jf - (2,5-dimethyl-l-pyrrolidinyl) -α, ot -diphenylbutyramidhydrοchlorid,

γ -piperidino- CK, cf-diphenylbutyramide-N-oxide,

γ - (2,5-dimethyl-l-pyrrolidinyl) - οι, ο ( -diphenylbutyramid,

y- (Dimethylamino) - c (, oi -diphenylvaleramide sulfate, γ - (2-methyl-l-piperidino) - 4 j oc -diphenylbutyramidhydrochlorid,

■ Jf-piperidino-Oj, <χ -diphenylbutyramide hydrochloride.

Other representative y- or CJ -amino-O ₁ /, Q ^ -diphenylalkanolamide compounds with repellent effects on animals include:

-jj — diethylamino- ο (, £? ς -diphenyl-N-methylbutyramide-

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γ -Diisopropylamino- οί, cK -diphenyl-N-methylbutyramidhydrο chloride,

y-dii-n-butylamino- ο (, oC -diphenyl-N-methylbutyramidhydrοchloride,

γ -diallylamino- ύί, dc -diphenyl-N-methylbutyramide hydrochloride,

• jp-di-2-butenylamino- c \ , o (-diphenylbutyramide hydrochloride (also ^ T -hexamethyleneimino- &, o { -diphenylbutyramide hydrochloride)

(^ - (2-methyl-l-pyrrolidinyl) - <^, cX -diphenylvaleramide, y -dimethylarnino- o (, a -diphenyl-N-methylvaleramide, ^ -dimethylamino-ei, ci -diphenyl-N-isopropylvaleramide-

hydrochloride (also the ^- ! T '- (2-isohexyl-l-pyrrolidinyl) compound),

^ v - (2-methyl-l-pyrrolidinyl) - cc, o ^ -diphenylbutyramide methobromide,

k iP-Dimethylamino- ot, (K -diphenyl-W-tert-butylvaleramide methobromide and

2Γ- (Piperidino) - ύί, o ^ - diphenylbutyramidraethobromide.

The compounds of formula I, including the specific compounds listed above, can be used in various concentrations from about 0.02% up to about 3% or more, or in amounts from about 0.1 mg to about 1 g, for repelling birds and others Animals are used.

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The compounds of the formula I, their acid addition salts and quaternary ammonium salts, their N-oxides and acid addition salts of N-oxides can according to the J.A.C.S., Vol. 79, pp. 4451-4456 (1957); I.e. Pages 4457-4462 and I.e. Pages 4462-4465 will.

The representative mineral acid addition salts include the hydrochlorides, hydrobromides, hydriodides, sulfates, Phosphates, hexafluorophosphates, nitrates, arsenates and fluosilicates. Representative organic acid addition salts are the acetates, propionates, benzoates, salicylates, glycolates, succinates, nicotinates, tartrates, maleates, Malates, oxalates, l, l-methylene-bis-2-hydroxy-3-naphthoates (pamoates), methanesulfonates ,. Dodecylbenzenesulfonate, Picrate, arsanilate and lactate.

The representative quaternary ammonium salts include the alkyl halide salts, e.g. methochlorides, Methobromide, methojodide, ethochloride, isopropobromide and the same; the alkenyl halides, e.g., allyl chloride, crotyl bromide, and the like; the alkyl nitrate salts; the alkyl sulfate salts; the alkyl phosphate salts and alkyl aryl sulfonate salts.

The active repellants according to the invention, namely the y- or Lo- amino-oc, o <-diphenylalkanoamides of the formula I, are effective in their pure form, as mixtures of pure compounds or as formulations with a diluent carrier with or without additives.

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A diluent carrier is often used to stretch the active agent and so the use or To facilitate application of concentrations of the active compound from a practical economic point of view.

A diluent carrier can be a liquid, a dispersible solid, or a combination be of liquid and solid. Accordingly, in the embodiment of the invention, the formulations Solutions of the active compounds in a solvent, suspensions, essentially homogeneous Powders, pastes, ointments, granules, emulsions and other useful forms known to the person skilled in the art are provided are.

The active compounds, namely the T "- or co amino <X, oC -diphenylalkanoamides, are in the form of their Free bases are insoluble in water, but in various organic liquids, for example ethers such as diethyl ether, alcohols such as ethanol, ketones such as acetone, cyclohexanone, and liquid chlorinated hydrocarbons, such as methylene chloride, soluble. On the other hand, the active compounds are in the form of their salts in changing Quantities soluble in water and other solvents and can be used with the appropriate practical Implementation of the method according to the invention can be used.

In general, suitable solvents include aromatic hydrocarbons such as benzene, Toluene, xylenes and naphthalenes, chlorinated aromatic

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- li -

Hydrocarbons, e.g. chlorobenzenes j paraffins, for example petroleum fractionsj animal and vegetable oil, for example soybean oil, linseed oil, Saffron Oil, Olive Oil, Lanolinj Ethanolaminej Whore thylformamide; Dimethyl sulfoxides and the like.

Among the dispersible solid carriers used to produce essentially homogeneous powders include china clay and bentonite, minerals in their natural state such as talc, pyrophyllite, Quartz, diatomaceous earth, puller earth, chalk as well Rock phosphate as well as the chemically modified minerals such as washed bentonite, precipitated Calcium carbonate or calcium silicate and colloidal silica.

A preferred, substantially homogeneous powder according to the present invention is a powder which contains one of the above-mentioned dispersible powders and a surface-active agent. The surface-active agent promotes the ability of the solid particles (powder) to be suspended in water, which is the usual liquid dispersible carrier material in agricultural practice. It also enhances the spray properties of an aqueous formulation when applied to a surface. Those skilled in the art refer to these preferred formulations as wettable powders. Such wettable powders can be made with a wide range of active ingredient concentrations. Concentrations can range from about 5 to about 90 percent by weight of the active ingredient. It

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Of course, other concentrations can also be used, but the goals of economic implementation are usually ver with the use of wettable powders with concentrations of about 20 to about 50% it is enough.

The representative surface-active agents which are useful for the preparation of the agents according to the present invention in the form of wettable powders include alkyl sulfates and sulfonates, alkylarylsulfonates, sulfosuccinate esters, polyoxyethylene sulfates, polyoxyethylene sorbitan monolaurate, alkylaryl polyether sulfates, alkylaryl aryl sulfates, alkylaryl polyether sulfates, alkylaryl aryl sulfates, alkylaryl polyether sulfates, alkylaryl aryl sulfates, alkylaryl polyether sulfates. sulfated fatty acids and esters, sulfated fatty acid amides, glycerol mannitan laurate , polyalkyl ether condensates of fatty acids, lignin sulfonates and the like. , Mixtures of Alkylarylsulfonaten and Alkylphenoxypolyäthoxyäthanolen (Triton X-151 »X-161 and X-171), eg approximately equal parts of sodium kerylbenzenesulfonate and Isoöatylphenoxypolyäthoxyäthanol, which ent about 12 ethoxy groups hold, as well as mixtures of Calciumalkylarylsulfojiaten and polyethoxylated vegetable oils (Agrimul NS). It is obvious that the above proposed surface-active sulfates sulfonates preferably in the form of their soluble salts, for example their sodium salts, for

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Use. All of these surfactants, at concentrations of about 1 % or less, are capable of reducing the surface tension of V / water to less than about AO dynes per cm. The dispersible powder compositions can ggbg. formulated with a mixture of surfactants of the types indicated above

The wettable powders are used in such a way that they can be placed in water for application to an object or dispersed a site so that animals sensitive to it are repelled and repelled by it. A watery spray can be applied to cornfields just before harvest or to horticultural, viticultural and forestry crops, for example cherry plantations, vineyards, conifers and the buds of flowering fruit trees Repels from birds are applied. Furthermore, aqueous sprays can be sprayed into trees in which there are a nesting place is located, so that the birds are driven away and induced to live with another, the human one Interest to gather more beneficial nesting place.

A suitable dispersible agent in powder form is obtained by adding 148 kg of Georgia clay, 2.04 kg of isooctylphenoxypolyethoxyethanol (Triton X-IOO) as a wetting agent, if 08 kg of one polymerize Sodium salt of a substituted, benzenoid long-chain Sulphonic acid (Daxad 27) as a dispersant and 51.3 kg of the active ingredient mixes and grinds »The The composition obtained in this way has the following percentage composition (unless otherwise stated), are the

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-ik-

Parts by weight:

Active ingredient - 25 %

Isooctylphenoxypolyethoxyethanol 1 %

Polymerized sodium salt of a substituted, benzenoid long-chain sulfonic acid 2 %

Georgia Alumina 72%

If this mixture is dispersed in a concentration of 4.54 kg per 379 liters of water, a spray preparation is obtained that contains about 0.3 % (3,000 ppm) of the active ingredient and is applied to trees, buildings, cornfields or where animals stay can"

Dispersants such as methyl cellulose, polyvinyl alcohol, iiatrium lignosulfonates can optionally be used and the like are incorporated into the dispersible powdery agents of the present invention will. Adhesives or adhesives, such as vegetable oils, naturally occurring types of rubber, Casein and others can also be incorporated. Corrosion inhibitors, for example epichlorohydrin, can also be used and anti-foaming agents such as stearic acid can be incorporated.

The agents according to the invention can be used to repel animals on crops, cornfields, herds, objects or Places to stay are applied by using aqueous sprays that come from a concentrated

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th solution of the active ingredients can be prepared. According to this embodiment of the invention, an active agent (especially the free bases) is preferably dissolved in a suitable inert organic solvent carrier. The solvent carrier is advantageously not miscible with water, so that an emulsion of the solvent carrier in water can be produced. For example, if a water-miscible solvent carrier, such as ethanol, is used, it will dissolve in water and any excess of γ- or te- amino-Oi, oc -diphenylalkanoamides will be eliminated from the solution. In an oil-in-water emulsion, the solvent phase is dispersed in the water phase and the dispersed phase contains the active ingredient. In this way, an even distribution of a water-insoluble active ingredient in an aqueous spray is achieved. A solvent carrier in which the compounds are soluble is desirable so that relatively high concentrations of the active ingredient can be obtained. Sometimes one or more solvent carriers, with or without cosolvents, can be used to obtain concentrated solutions of the active ingredient; The primary consideration here is to use a water immiscible solvent for the active ingredient that will hold the compound in solution over a range of concentrations useful in repelling the animals.

The emulsifiable concentrates according to the invention are therefore obtained by the active ingredient -

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part and a surfactant in a substantially water immiscible solvent carrier (i.e. a solvent vehicle that is immersed in water to an extent of less than 2.5 vol JiS at temperatures is soluble in an order of magnitude of 20 to 30 C), for example cyclohexanone, methyl propyl ketone, summer oils, Ethylene dichloride, aromatic hydrocarbons,

fc such as benzene, toluene and xylene as well as high-boiling Petroleum hydrocarbons, such as kerosene, diesel oil and the like, dissolves. If desired, can be a secondary solvent, such as methyl ethyl ketone, acetone, isopiopanol and the like, be incorporated with the solvent carrier to increase the solubility of the active ingredient. Aqueous emulsions are then made by mixing with water to provide any desired concentration of the active Component. The surfactants that are used in the aqueous emulsions of the invention are of the types listed above. If necessary, mixtures of

f surface-active agents are used.

Advantageously, the concentrations of the active ingredient in the emulsifiable concentrates within a range of about 5% by weight to about 50% by weight, preferably about 10% by weight to about 50% by weight lie. A concentrate containing 20% by weight of the compound in solution in a water-immiscible solvent of the type indicated above can be mixed with an aqueous medium in proportions of 13 ml of the concentrate are mixed per 3 »79 1 of the medium,

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so that a mixture is obtained that contains 700 parts of the active Contains constituents per million parts of the liquid carrier material. Mixing is done in the same way from 0.95 liters of a 20 percent concentrate with 151 liters of water to about 1.20QC ppm of the active ingredient. In the same way, more concentrated solutions of the active ingredient can be made.

The concentrate compositions according to the invention, which are used in the form of aqueous dispersions or emulsions are to be, may also contain a humectant, that is, an agent that delays drying of the composition in contact with the material to which it is applied. to suitable humectants include glycerin, diethylene glycol, dissolved lignins, such as calcium lignin sulfonate and the same.

Example 1:

A dispersible powder concentrate of the following percentage composition:

Tf- (2-methyl-l-pyrrolidinyl) - o <, <tf diphenylbutyramide 45.8 %

Polymerized sodium salt of a long chain substituted benzoid Sulphonic acid (Daxad 27) 9.2%

Kaolinite 45.0 %

v / urde by mixing 250 g of f - (2-methyl-l-pyrrolidinyl) -ot, oC -diphenylbutyramide, 50 g of a polymer

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Sated sodium salt of a substituted, benzenoid long-chain sulfonic acid (Daxad 27) and 245 S kaolinite. The mixture was ground to a particle size of 5 to 30 microns. It was suspended in 37.9 liters of water to give an aqueous spray which contained 6,500 parts per million of the active ingredient for use on crops or cornfields to repel birds.

Example 2;

An emulsifiable concentrate of the following percentage composition:

g- - (2,5-Dimethyl-1-pyrrolidinyl) - (X> Q ^ -diphenylbutyramide HCl

Technically pure alkylnaphthalene mjt a boiling point of 238 to 293 C (Velsicol AR5O)

Xylene
fc isopropyl alcohol

Ethylene dichloride.

Mixture of alkylarylsulfonates and alkylphenoxypolyethoxyethanols (Triton X-151)

was obtained by mixing 6.8 kg of χ- (2,5-dimethyl-lpyrrolidinyl) -o (., flC-diphenylbutyramide HCl, 8.9 kg Velsicol AR50, 7.9 kg xylene, 7.9 kg isopropyl alcohol, 11.5 kg of ethylene dichloride and 2.3 kg of Triton X-151 were produced.

15.0 % 19.7 % 17.4 % 17.4 % 25.4 % 5.1 %

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30 kg of the concentrate were mixed with 37.9 1 of water and resulted in a spray emulsion containing 11,000 ppm of T- (2,5-dimethyl-1-pyrrolidinyl) -cC ι <k -diphenylbutyramide-HCl for application to seeds to ward off Contained birds.

Example ^;

An emulsifiable concentrate of the following percentage composition:

if-Dimethylamino-et, oi -diphenylvaleramide- ^ 0.0 % sulfate

Technically pure alkylnaphthalene with a 13 »7 % boiling point from 238 to 293 ° C (Velsicol AR50)

Xylene 12.3 %

Isopropyl alcohol 11.3%

Ethylene dichloride 17.7 %

Mixture of alkylarylsulfonates and alkyl 5.0% phenoxypolyethoxyethanols (Triton X-151)

It was obtained by mixing 18.1 kg of dimethylamino-cc, ^ L "diphenylvaleramide sulfate, 6.2 kg of Velsicol AR50, 5.5 kg of xylene, 5.1 kg of isopropyl alcohol, 8.0 kg of ethylene dichloride and 2.2 kg Triton X-I5I manufactured.

0.76 kg of the concentrate mixed with 37.9 liters of water produced a spray emulsion containing 8,000 ppm of IJ- -Dimethylaminoof. , «Χ -diphenylvaleramide sulphate contained on resting places or objects to ward off animals.

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Example 4 »

A wettable powder concentrate with the following percentage composition:

y -Piperidino- <Λ, cx-diphenylbutyramide- ^ O% N-oxide

Kaolinite clay (finely divided) Zf6 %

Sodium salt of condensed mono - 4 % naphthalenesulfonic acid (Lomar D)

was prepared by mixing 50 g of Jf-piperidino- o <, oi -diphenylbutyramide-N-oxide, 46 g of kaolinite clay and 4 g of Lomar D. The mixture has been ground to an average particle size of 5 to 30 microns and can be used to coat seeds.

Example 3?

The active ingredient, namely # ~ - (2,5-dimethyl-lpyrrolidinyl) -o (,, c < -diphenylbutyramidhydrochloride) was dissolved in a 40 percent solution of isopropyl alcohol in water and the solution was sprinkled over sugar millet grains while the Grains were shaken and mixed. The amount of spray was measured to apply about 0.2% by weight of the active ingredient. After drying, the coated grains were sprinkled over a sown field to repel the birds Spreading about 3 »8 1 per 0.4047 ha within a strip about 60.96 m wide, especially on the edges of large fields, repels hungry flocks of birds.

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The same repelling effect was achieved by adding a portion of y- (2-methylpiperidino) - ot, o (-diphenylbutyramide hydrochloride and part of ^ - (2-methyl-lpyrrolidinyl) -α »Et -diphenylbutyramide in isopropyl alcohol solves.

In the same way, those used according to the invention can be used free basic compounds, their N-oxides, their quaternary ammonium salts and N-oxide acid addition salts or mixtures thereof can be used as active agents to achieve the same repelling effect.

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Claims (10)

Claims; 1. Means for repelling animals, especially birds and mice, consisting of a, if necessary. fr- or cu -amino- oC, o (, -diphenylalkanoamide of the following general formula as active ingredient in a mixture with conventional diluents and additives: "3 V C-N in which R and Rp, independently of one another, are hydrogen atoms or lower alkyl groups with 1 to 1 carbon atoms, η is the integer Z or 3j R,,. independent of one other, lower alkyl groups with 1 to Zf carbon atoms, Mean alkenyl groups with 3 or Zf carbon atoms, and Ε-, as well as R, together with the connected '3 k - -NC ^ -atom form a saturated heterocyclic amino group with 5 to 7 ring atoms and a total of not more than 10 carbon atoms, or their acid addition salts 2098 10/1972 and quaternary ammonium salts, N-oxides and N-oxide acid addition salts. 2. Means according to claim 1, characterized in that η is 2 and R and Rp are hydrogen atoms mean. 3. Composition according to claim 2, characterized in that R ^, and R, together with the connected -N ^ atom form a saturated heterocyclic amino group. Zf. Means according to claim 3 »characterized in that that the saturated heterocyclic amino group is a pyrrolidinyl radical. 5. Composition according to claim k> characterized in that the active ingredient <T- (mono-lower-alkyl- or di-lower-alkyl-1-pyrrolidinyl) - C {, o ( -diphenylbutyramide) is. 6. Agent according to claim 5, characterized in that the active ingredient is if- (2-methyl-l-pyrrolidinyl) -Of, d -diphenylbutyramide. 7. Agent according to claim 5, characterized in that the active ingredient is γ - (2,5-dimethyl-l-pyrrolidinyl) · Qj , o (-diphenylbutyramide. 8. Composition according to claim 3> characterized in that the saturated heterocyclic amino group is a piperidino group. 209810/19 72 2U0862 9. Composition according to claim 8, characterized in that the active ingredient γ * - (mono-lower-alkylpiperidino) -c (, ac -diplienylbutyramide is. 10. Means according to claim 9> characterized in that the active ingredient "^ - (Z-methylpiperidino) - ^, oi - is diphenylbutyramide. For: The Upjohn Company Lawyer 209810/1972