CH654465A5 - Attractant preparation for male winter seed owls. - Google Patents

Description

The invention relates to an attractant preparation for selectively attracting male winter seed owls, insect trap containing this preparation, a method for selectively attracting and capturing male winter seed owls, and furthermore a method for preventing the mating of these insects using the air space saturation method.

As is known, the winter seed owl (Scotia segetum) is a widespread pest, which eats several plant species and causes annually recurring damage in the production of almost all crops, in particular tobacco, sugar beets, other types of vegetables and cereals. To combat this pest, mainly phosphoric acid ester derivatives have been used so far; However, all such control agents have the disadvantage that they have no selective action and are also extremely toxic to humans. The use of phosphoric acid esters against the winter seed owl is also made more difficult by the fact that the older caterpillars live a hidden way of life in the soil and are difficult to access for the insecticidal agent.

The environmental problems encountered when using the conventional chemical control methods can be eliminated in the control of butterflies if natural sex attractants, so-called sex pheromones, of the preparations containing the butterfly species to be controlled are used as control agents. Such sex attractants are produced and excreted by the female animals; the male butterflies of the same species can then use this fragrance to find the females and mate with them.

The sex attractants can basically be used in plant protection in two different ways.

According to the first procedure, sex attractants are exposed as bait-containing traps, which trap the male butterflies attracted by the active ingredient. In this way, information about the occurrence of the pests can be obtained immediately, so that one can find out in advance about the expected cause of the damage. This procedure has the advantage over other procedures, also based on the use of traps, that only traps selected in the given case are caught in the sex attractants as bait, while practically all of them fly at night in the light or UV traps Insects are caught. The sex attractants as bait-containing traps generally indicate the beginning of swarming of the pests more sensitively than the light traps (see Manu and co-workers, Switzerland. Z. Obst, Weinbau 81 [1972], pages 337 to 344). If the immediate vicinity of the traps is then treated with an insecticidal agent, most of the male butterfly population attracted to them is killed in the "extermination zones" thus created; the risk of environmental pollution with the insecticidal agent is restricted to these destruction zones, ie largely reduced.

By using the other procedure, the so-called "procedure of air space saturation", the male butterflies can be disturbed in finding the females and thus the mating of the animals can be prevented. In this case, a larger amount of the sex attractant is evenly distributed in the air space throughout the plant crop to be protected, so that the male animals can feel the presence of the sex attractant everywhere; they are so to speak confused and cannot find the females they are looking for. With these relatively small amounts of sex attractants, which

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only a fraction of the usual doses of the classic insecticide active ingredients (compare W. L. Roenols and R.T. Cardé, Ann. Rev. Entomol. 22 [1972], pages 377 to 405).

By using traps containing the sex attractant of the winter seed owl as bait, this pest can also have the disadvantage of the previous control process technology that the onset of the pests was difficult to recognize in good time and the control could therefore only be started when the older caterpillars were in the inner parts of the plant, which were practically inaccessible for the classic insecticide active ingredients, had already exerted their harmful effect.

In addition to the high selectivity of the sex attractants, especially when used according to the air space saturation procedure, there is an important further advantage that these active substances have a non-toxic effect on vertebrates (MC Birch [Ed]: Pheromones, North Holland Publishing Co., London-New- York, 1974, page 495).

The sex pheromone of the winter seed owl was produced by Best-man and co-workers (Angew. Chemie 10, 815-816 / 1978). The structure of the pheromone was identified as 5 (Z) -decen-l-ol acetate (compound of the formula I)

CH3 - (CH2) -C = C - (CHp) "-CH9 -O-C-CH0

J * J I I 2 3 2 Ii 3

H H 0 (I)

specified. Further experiments have found that this pheromone consists of two components - namely 7 (Z) -dode-cen-l-ol-acetate (compound of the formula II)

CH3- (CH2) 3-c = c- (CH2) -CH2-O-C-CH3

H H 0 (II)

and 9 (Z) tetradecen-l-ol acetate (compound of the formula III)

ch3- (CH2) 3-ç = ç- (CH2) 7-CH2O -C-CH3

H H 0

(III)

exists (Belgian Patent No. 886 800).

According to the invention, it was found that the 5 (Z) -decen-l-ol acetate of the formula I has only a very low attracting effect in the field. A mixture of the 7 (Z) -dodecen-l-ol-acetate of the formula II and the 9 (Z) -tetradecen-l-ol-acetate of the formula III attracts the male individuals of the winter seed owl, but they also fall into the trap male individuals of other related species of owl. This makes it difficult to evaluate the capture.

The invention is based on the knowledge that one of 7 (Z) -dodecen-1-ol-acetate of the formula II, 9 (Z) -tetradecen-1-ol-acetate of the formula III and 5 (Z) -decen-1 -ol-acetate of the formula I existing combination has a synergetic effect and exerts a locative effect on the male winter seed owls, which has the effectiveness of the 5 (Z) -decen-l-ol acetate and that in Belgian Patent No. 886 800 described, consisting of two components preparation far exceeds. The preparation according to the invention is so largely specific that, in the insect trap, it attracts and captures the male individuals practically exclusively to the winter seed owl.

The invention relates to an attractant preparation for selectively attracting male winter seed owls (Scotia segetum), characterized in that it contains, as active ingredient, a mixture of 1-98% by weight of 5 (Z) -decen-l-ol acetate of the formula 1, 1-98% by weight of 7 (Z) -dodecen-l-ol-acetate of the formula II and 1-98% by weight of 9 (Z) -tetradecen-l-ol-acetate of the formula III, optionally together with liquid and / or solid diluents and / or other auxiliaries.

The preparation according to the invention advantageously contains 5-90% by weight of compound of formula I, 5-90% by weight of compound of formula II and 5-90% by weight of compound of formula III.

The attractant preparation according to the invention expediently contains inert solvents, especially hydrocarbons, in particular n-hexane, and / or halogenated hydrocarbons, in particular dichloromethane and / or viscous liquids, in particular sunflower oil and / or paraffin oil, as diluents. Further examples of inert solvents are alcohols, such as methanol, and ketones, such as acetone. However, any organic solvent which is inert to the two active substances and in which they are sufficiently soluble is suitable for the solutions.

Thus, the attractant preparation according to the invention can be present as a solution of the three active ingredients in an inert solvent, which is advantageously prepared in the form of capsules or microcapsules.

Such attractant preparations according to the invention can be used particularly advantageously in winter seed owl traps. The solvent evaporates quickly from the trap and the remaining combination of active substances gradually exerts its locative effect through slow evaporation.

In order to make the evaporation of the active ingredients uniformly slow, the attractant preparation according to the invention can advantageously contain various viscous, low-volatility liquids, such as sunflower oil, olive oil, paraffin oil and / or mineral oils, which are inert to the active ingredients. These liquids do not influence the attracting effect at all, but keep the evaporation rate of the active ingredients at a constant level, so that the reduction in activity that might otherwise occur when using high active ingredient concentrations can be avoided. However, the presence of the viscous liquid is not absolutely necessary to achieve the desired effect.

An attractant preparation according to the invention which contains 12 to 67% by weight sunflower oil, 80 to 30% by weight n-hexane and 8 to 3% by weight of the active compound combination according to the invention has proven to be advantageous. An amount of this solution which corresponds to an active ingredient dose of 0.001-3.0 mg is preferably used.

Also particularly advantageous is an attractant preparation according to the invention which contains a solution which contains 50 to 90% by weight of an inert solvent, in particular n-hexane or dichloromethane, and 50 to 10% by weight of the active ingredient combination, which in a suitable form, for Example in rubber, rubber or polyethylene capsules is sucked up, prepared. Of these, too, an amount corresponding to an active ingredient dose of 0.001-3.0 mg is preferably used.

As an advantageous possibility, the attractant preparation according to the invention can be used in winter seed owl traps for attracting and catching male winter seed owls (Scotia segetum).

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As another advantageous possibility, the attractant preparation according to the invention can be used to prevent the mating of winter seed owls (Scotia segetum) according to the known method of air space saturation. The active ingredient mixture of the attractant preparation according to the invention can advantageously be emitted into the airspace at speeds of 1.0 to 30.0 mg / ha / hour, preferably 5.0 to 20.0 mg / ha / hour.

The invention furthermore relates to an insect trap for selectively attracting and capturing male winter owls, characterized in that they are present in an amount of 0.001-3.0 mg - preferably 0.005-0.5 mg

- Contains a composition according to the invention, optionally dissolved in an inert solvent or in a viscous liquid and / or formulated in a capsule.

The invention further relates to a method for attracting and capturing male winter seed owls, characterized in that these insects are exposed to the action of the above trap.

The invention further relates to a method for reducing the pairing of winter seed owls, characterized in that an inventive composition at a rate of 1.0-30.0 mg / hour / ha - advantageously 5.0-20.0 mg / hour / ha - emits into airspace.

The preparation of the 7 (Z) -dodecen-1-ol-acetate of the formula II and the 9 (Z) -tetradecen-1-ol-acetate of the formula III was described in Belgian Patent No. 886,800.

The 5 (Z) -decen-l-ol acetate of the formula I can be prepared in a manner known per se from the propargyl alcohol of the formula IV

R-0-CH2-CsCH (IV)

(R is hydrogen) can be produced as follows:

The hydroxyl group of the propargyl alcohol is masked. From the compound of formula IV thus obtained (in which R is the 2-tetrahydro-pyranyl or 1-ethoxyethyl group) an anion is formed with the aid of a strong base (advantageously alkyl lithium), which - without isolation

- With a compound of general formula V

CH3-CH2-CH2-X (V)

(where X is chlorine, bromine, iodine, tosyloxy or mesyloxy). From the compound of general formula VI thus obtained

R-0-CH2-C = C- (CH2) 2-CH3 (VI)

(in which R has the above meaning) the protective group is removed by acid catalysis and the compound of general formula VI (in which R is hydrogen) is reacted with the potassium salt of 1,3-diamino-propane. The hydroxyl group of the compound of the general formula VII isolated from the reaction mixture

R-0-CH2- (CH2) 3-C = CH (VII)

(R stands for hydrogen) is masked. With the aid of a strong base (preferably alkyl lithium), an anion is formed from the compound of general formula VII (in which R has the above meaning) thus obtained, which anion is isolated with a compound of general formula VIII without isolation

CH3- (CH,) 2-CH2-X (VIII)

is implemented (in which X has the meaning given above). The protective group of the compound of the general formula IX isolated from the reaction mixture

R-0-CH2- (CH2) 3-C = C- (CH2) 3-CH3 (IX)

(wherein R has the above meaning) is removed by acid catalyzed hydrolysis and the resulting compound of general formula IX (wherein R is hydrogen) is acylated with an acetylating agent - preferably a mixture of acetic anhydride and pyridine). The compound of formula X thus obtained

CH3-C-0-CH2- (CH2) 3-C s C- (CH2) 3-CH3 (X)

O

is hydrogenated in the presence of a catalyst of moderate activity, preferably palladium / barium sulfate, to give the 5 (Z) -decen-1-ol acetate of the formula I.

The effect of the preparation according to the invention is demonstrated by the following test experiments.

The first trial was carried out in Pestimre, between June 16 and July 3, 1980 on a cabbage field of about 50 hectares. The traps used consisted of two plastic panels, each curved in the middle like a tent roof, each measuring approximately 20 cm x 30 cm. The panels were linked at their corners so that the roof, which was curved like a tent roof, was perpendicular to each other. The inner part of the lower plate was lubricated with an adhesive to catch the flying insects. The bait was hung from the inside in the middle of the top plate. The traps were placed 25 m apart and at a height of 0.5 m. One trap was used per treatment.

The second trial was carried out in Törökbälint, in an orchard of about 500 hectares, between July 17 and August 18, 1981. The above traps were hung at a height of about 1.5 mm in the crown of the trees. Three cases were operated per treatment.

The caught animals were collected weekly and determined according to their type and genus. The results obtained were statistically evaluated using the “Duncan Multiple Range Test”.

In the first experiment, male winter seed owls were captured using only the 7 (Z) -dodecen-1-ol acetate and 9 (Z) -tetradecen-1-ol acetate mixture and the three component composition. The 5 (Z) -decen-l-ol acetate itself did not have an attracting effect. The three-component head position attracted almost four times more male winter owls than the mixture consisting of 7 (Z) -dodecen-l-ol-acetate and 9 (Z) -tetradecen-l-ol-acetate.

The results obtained are summarized in Table I.

In the second experiment, the 5 (Z) -decen-1-ol acetate gave about the same result as that of 7 (Z) -dodecen-1-ol-acetate and 9 (Z) -tetradecen-1-ol-acetate existing mixture. The number of male winter seed owls trapped in the trap containing the three components (I -I- II + III) is more than ten times higher; this value is significantly larger (P = 5%).

The results obtained are given in Table II.

The average values labeled with identical letters (a and b) do not differ significantly from each other with P = 5%.

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It can be seen from the two tables I and II that the composition according to the invention, consisting of three components, has a significantly stronger attracting effect on male winter seed owls than the two previously known preparations. The synergetic effect demonstrated in the second experiment is particularly convincing. The invention is illustrated by the examples below.

Table I

Compound I (1.0 mg)

4: 1 (% by weight) mixture of II and III (1.0 mg)

4: 1: 2.5 (% by weight) mixture of II, III and I (1.5 mg)

Average number of male winter seed owls captured

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Table II

Compound I Compounds II + III Compounds II + III

(1.0 mg) (4: 1 wt%) + I wt (1.5 mg)

1mg 0.1mg 0.01mg 1: 1: 1

Average number of male winter seed owls captured 7a 0a 7a 8a 127b

example 1

There were 120 parts by weight of sunflower oil or paraffin oil with 80 parts by weight of n-hexane and 8 parts by weight of an active ingredient mixture of 4 parts by weight of compound of formula II, 1.5 parts by weight of compound of formula III and 2.5 parts by weight of compound of formula I (ie weight ratio 4: 1, 5: 2.5) mixed. An amount corresponding to an active ingredient combination of 0.1 to 0.3 mg was weighed into the correspondingly designed part of a trap, for example a rubber capsule or a polyethylene capillary, from the solution obtained. The solution of the active ingredient combination could either be added to the glue used to trap the insects or it could be absorbed by textiles or natural or artificial porous materials.

Example 2

The procedure was as described in Example 1, but with the difference that 10 parts by weight of paraffin oil, 1 part by weight of butylated hydroxytoluene (2,6-ditert.-butyl-4-methylphenol), 1 part by weight a light stabilizer, for example Uvizon®, 80 parts by weight of n-hexane and 8 parts by weight of the active ingredient mixture (2.66 parts by weight of compound 1.2.67 parts by weight of compound II and 2.67 parts by weight). Parts of compound III) were used.

Example 3

10 parts by weight of an active ingredient combination of 4 parts by weight of compound of the formula II, 1 part by weight of compound of the formula III and 3 parts by weight of compound of the formula I (that is to say a weight ratio of 4: 1: 3) were obtained at 90 Parts by weight of n-hexane are mixed and 1 to 2 mg of the active substance combination containing amounts of this solution are weighed in traps. The active ingredient solution was allowed to soak up in polyethylene of the polypropylene capillaries with an inner diameter of 0.3 mm.

Example 4

There were 9 parts by weight of an active ingredient combination of 3 parts by weight of compound I, 3 parts by weight of compound II

25 and 3 parts by weight of compound III homogenized with 91 parts by weight of silicone oil and added to the adhesive used in traps in such an amount that 1 to 5 mg of active compound mixture got into the traps.

Example 5

A flannel strip with a width of 2 cm was impregnated with the active ingredient combination solution prepared according to Example 3 in n-hexane. After evaporation of the 35 n-hexane, the strip was welded between polyethylene foils with a thickness of 0.1 to 0.5 mm. The form thus produced was applied in a uniform distribution over the area to be protected against the insects in such a way that 1.0 to 30 mg / ha / hour of active compound mixture reached the air space.

Example 6

The procedure was as in Example 5, but with the difference that the active compound combination solution in n-hexane, paraffin oil or odorless kerosene was added in such an amount that the solution obtained was 30 to 50 parts by weight of n-hexane and 40-60 Parts by weight of paraffin oil or kerosene contained.

50

Example 7

The procedure was as described in Example 1, with the difference that an active ingredient mixture of 4 parts by weight of compound, 1.2 parts by weight of compound II 55 and 2 parts by weight of compound III was used (that is, weight ratio of the active ingredients = 4: 2: 2).

Example 8

The procedure was as described in Example 1, but with the difference that an active ingredient mixture of 1 part by weight of compound I, 5 parts by weight of compound II and 2 parts by weight of compound III was used (that is to say the weight ratio of the active component 1 : 5: 2).

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Claims (10)

654 465 1-98% by weight of 7 (Z) -dodecen-1-ol acetate of the formula II CH «- (CH0) -C = C- (CH0) _-CHo0-C-CH„ J ~ 3 [j ~ - n 3 H H 0 (II) and 1-98% by weight of 9 (Z) tetradecen-1-ol acetate of the formula III CH „- (OHL,) q-C = C- (CH0) _-CH0 -0-C-CH_ J - J (i ~ / - u 3 H H 0 (III). contains. 2. attractant preparation according to claim 1, characterized in that it contains the active ingredients together with liquid and / or solid diluents and / or other auxiliaries. 2nd PATENT CLAIMS 1. Attractant preparation for selectively attracting male winter seed owls, Scotia segetum, characterized in that it contains a mixture of 1-98% by weight 5 (Z) -decen-l-ol-acetate of the formula I as active ingredient CII - (CH0) "-C = C- (CH0)" -CIi0 -0-C -Cli J - J i I - J - i, 3. attractant preparation according to claim 1 or 2, characterized in that it is a mixture of 5 to 90 wt .-% compound of formula I, 5 to 90 wt .-% compound of formula II and 5 to 90 wt .-% compound of Formula III contains. 4. attractant preparation according to one of claims 1 to 3, characterized in that it contains an inert diluent, advantageously n-hexane or dichloromethane, and / or a viscous liquid, advantageously sunflower oil or paraffin oil. 5. An insect trap for selectively attracting and capturing male winter owls, characterized in that it contains in an amount of 0.001 to 3.0 mg of an attractant preparation according to claim 1 or 2. 6. Insect trap according to claim 5, characterized in that it contains 0.005 to 0.5 mg of an attractant preparation according to claim 1 or 2. 7. Insect trap according to claim 5 or 6, characterized in that it contains the attractant preparation dissolved in an inert solvent or in a viscous liquid and / or formulated in a capsule. 8. A method for attracting and capturing male winter owls, characterized in that these insects are exposed to the action of an attractant preparation according to claim 1. 9. A method for reducing the mating of winter seed owls, characterized in that an attractant preparation according to claim 1 is sent into the airspace at a rate of 1.0 to 30.0 mg / hour / ha. 10. The method according to claim 9, characterized in that one sends the attractant preparation at a rate of 5.0 to 20.0 mg / hour / ha in the air space.