FI66109C - FOERPACKNINGS- ELLER OEVERDRAGNINGSMATERIAL INNEHAOLLANDE ETT AKTIVAEMNE FOER BEKAEMPNING AV INSEKTER OCH KVALSTER - Google Patents

Description

1 66109

The present invention relates to a packaging or coating material containing a pyrethrin-type compound as an active ingredient.

The invention is characterized in that the active ingredient consists of at least one compound of the general formula (I) wherein Y is a group (I)

A

H3C / CH3

X

H / \ 20 \ / z 'where Z is a group

XK

N-CH- * 2 wherein X1 and X2 represent a chlorine or bromine atom, or Z is a group X-.

•> rr X5 X5 35 2 66109 where and denote a chlorine or bromine atom, in which case the group (I) is in the cis or trans configuration

A

and optically active, and that the alcohol moiety of Compound I has the configuration of (S). The invention relates in particular to a material as defined above, which is characterized in that the compound of general formula (I) contained therein is (1R cis) 2,2-dimethyl-3- (2,2-dibromovinyl) -cyclopropane-1-carboxylic acid. (S) cX-Cyano-3-phenoxy-benzyl ester (Compound A).

More particularly, the invention relates to a material as described above, characterized in that it consists of paper, contains 10 mg to 1 g of active substance per square meter and in particular contains 10 mg to 500 mg of (1R cis) 2,2-dimethyl-3 - (2,2-Dimethyl-3- (2,2-di-bromo-vinyl) -cyclopropane-1-carboxylic acid (S) -? - cyano-3-phenoxy-benzyl ester (Compound A) per square meter.

The paper used is impregnated on one or both sides, depending on its intended use, with a spray-20 wettable powder containing a compound of formula I, e.g. 2.5% of compound A, and a carrier formed from inert stearic acid-treated calcium carbonate.

The invention relates in particular to a paper material as described above, which is characterized in that the impregnation of the paper with the active substance is carried out on both sides.

The papers treated according to the invention may contain, as already mentioned above, 10 mg to 1 g / m of active ingredient. More specifically, they may contain from 10 to 120 2 mg / m 2 of compound A.

66109

The papers used according to the invention can be of various types. Especially chemically pulp-free glued paper made of pulp with an acidic pH can be used.

The invention also relates to a material as described above, characterized in that it consists of a plastic film, contains 10 mg to 2 g of active substance per square meter and in particular contains 10 mg of 1 g of compound A per square meter.

Plastic films are impregnated according to the invention as a mass impregnation by hot addition of pyrethrin compounds either dissolved in 10 g / l acetone containing 1 ppm acetic acid or dissolved in 75 g / l xylene, or 1% diluted as a powder by plastic extrusion.

The invention therefore relates to a material as described above, which is characterized in that the impregnation of the plastic film with the active substance is carried out as a mass impregnation.

The plastic films according to the invention preferably contain 2 to 40 to 600 mg / m 2 of active ingredient and in particular 40 to 350 mg / m 2 of compound A.

The plastic films used according to the invention can be of various types. In particular, polyethylene films can be used.

Due to the compounds of formula (I) impregnated in them, the materials according to the invention have pesticidal, in particular insecticidal and acaricidal properties.

66109

The invention therefore also relates to the practical application of the material described above, i.e. paper or plastic film, in which case the packages or coatings made of said material have insect repellent or insect repellent properties.

Experiments with houseflies and Culex pipiens using paper or plastic films treated with Compound A show in particular the insect repellent and insect repellent effect of the materials according to the invention.

Examples of these experiments are given in the experimental part of the text below.

The materials of the invention also have mite repellent and mite repellent properties.

The papers or plastic films treated according to the invention can be used in particular for the production of sacks for the packaging of seeds, for the production of bags for the storage of perishable goods and for the production of bags for the storage of surgical instruments when protection against parasitic diseases is desired.

The papers of the invention can be used to make insect-protected book pages or to coat the walls of homes for the purpose of repelling and destroying insects like flies and mosquitoes and the like.

The compounds of formula (I) and in particular compound 30a are well known in pesticide chemistry.

5 66109

Example 1: Paper impregnated with Compound A 2 A glued paper made of 2 m of bleached chemical cellulose pulp with an acidic pH was used.

5 Impregnation was carried out at the end of the preparation by spraying on one side of the paper a wettable powder containing 2.5% of Compound A and an inert carrier formed from stearic acid-treated calcium carbonate. The paper was allowed to dry in air for 10 days. The main active ingredient was used in an amount such that the paper contained 100 mg of Compound A per square meter.

Example 2: Plastic film 2 impregnated with Compound A A 5 m polyethylene film 15 was used, which was impregnated hot at the time of extrusion of the entire mass of plastic mass by adding Compound A dissolved at a concentration of 10 g / liter in acetone, which also contained one ppm of acetic acid. Compound A was used in such an amount that the polyethylene film contained 130 mg of Compound A per square meter.

Investigation of the insect repellent effect of the materials according to the invention a) Insect repellent effect of the paper according to the invention on insect repellents 25 Insect repellent paper containing 65 mg or 30 mg of compound A per square meter was used. This paper was impregnated by spraying on its other side 2.5% of Compound A, i.e. (1R cis) -2,2-dimethyl-3- (2,2-dibromovinyl) -cyclopropane-1-30 carboxylic acid (S) -cyano-3 -phenoxybenzyl ester and a wettable powder containing an inert carrier formed from stearic acid-treated calcium carbonate.

Neutral-neutral paper (thus not containing compound 6610109) was used as a reference material. This paper was a wood-free glued paper made of bleached chemical pulp with an acidic pH. This same paper had also been used for impregnation with Compound A.

A 13.5 cm wide and 30 cm long piece of paper (area 2,400 cm) was placed inside a 1 liter container and the walls of the can were covered with this paper. After the flies were placed in the can, it was closed with a torn lid and the insects were left for an hour in Koskelo with paper attached to the walls of the can, the insects were removed from the can and placed in containers serving food and water.

Checks were performed during the contact time (after 30 minutes) and at the end of the contact time at 15 (after 60 minutes) in order to find out

Knock Down Effect (percentage of insects that faded in 60 minutes).

Other checks were performed after two hours, four hours, and 24 hours (lethal effect + Knock Down effect). The experiments were performed three times in sets of 25 individuals.

The results of the experiments are summarized in the following table: 7 661 09 (.. ,,,.: Doses:% folded: Death.; K.D)) From the beginning, .. .lei-. +)): g /. -suus K. D 'kill- (V: *. „., * 4: va vai- \ |:: 30 mn 60mn 2h Uh ^:;] cutus j (Processed: 30: 100 1100: 10 ° J 100: 10 °: 10 ° 5100 ^ 5 V paper * · · · 5 '. · · -) (: 65: 100 s 100: 100: 100: 100: 100: 100) i -; - i— (Neutral-: 5 s:::::) (paper::; s::::) (· (comparative · sh 3i 0: 3 »2j 2, -1: 1,3: 0 · 0 | (: * t !! ! 5:) (_i_? »:::; Tl

Conclusion: Papers treated with the impregnation concentrations used showed a significant insect repellent effect.

b) Anti-housefly effect of the plastic film according to the invention This experiment was carried out analogously to the method used in a) above.

20 Polyethylene film was used. This film can be impregnated over its entire mass by hot addition of compound A dissolved in 10 g / liter of acetone at the time of extrusion of the plastic mass, which also contains one per mille of acetic acid.

The results obtained in the experiments are summarized in the following table: 8 66109; p—, '·,:) (Start! Doses: * bent *: KD | (:: 30: 60: 2h: Uh s 2Uh: KD: callus) \ mil mn (S f Processed. ...... (

(plastic film 325 j 100 | ΙΟΟ; 100 *. 100 *. 100; 100; 100 J

(· 130: 100: 100: 100: 100: 100: 100: 100) 1Q t: 65: 100: 100.-100: 100: 96.0: 100: 96.0 | (Reference material: -: 0 \ 0 MC, 7-j 6-; 7; 0: 0: 0 j (rial,: _:;::; _ · _ · _ ^ 15 Conclusion: At the doses used, the plastic film showed significant insect deterrent effect.

c) The anti-Culex pipiens effect of the paper according to the invention

The experiment was performed in a) analogously to the experiment performed with houseflies 20 but using sets of 20 individuals and repeating the experiment three times.

\ Format .Doses x. ^ faded: lei- ~:: K · D · 1

(.mg / ra2 .---; -; -— jsuus% ’* lethalJ

25 (5:30, lin: 60mrt 2lh: kh: 24h: KD .effect (Treated; 100 * 55.0; 88.3:. 90.0: .95.0: 100: 88.5 * 100 (\ paper: _: _ · _ · _::) (: 60 mg / m2 · 56.7: 90.0: 100: 100: 100: 90.0: 100) I: ::::: ·: 1 -i -; -; -; -; -; -; -; -

Processing:::::::: J

mätön pape- J _ | 3.3; 3.3; 5.0s 6.7! 8.3! 0: O! ri. :::::::) _L__ ♦ * 1::::)

Conclusion: At the doses used, the impregnated paper with compound A showed a significant insect repellent effect.

9 66109 d) Anti-Culex pipiens effect of the plastic film according to the invention This experiment was carried out analogously to the paper experiment in c) above.

5 The results of the experiment are summarized in the following table:

Start i! * stuck: 1 ^ 1 ^! li ') in (: nig / nr. .suus%.. lethal ^ (___:: 30inn: 60mn: 2 h PTh ”: 2b. h: K. D:) (: II 5 i: 5 x (: 325 : 10.0: 70.0: 93.3: 1005 ... 100: 70.0: 100):,) 1 iii::: :-)

{Treated: 130: 10.0: 61.2: 83.3: 95.0 100: 61.7 s 100 J

15 -J-5-S-J-Σ -: - 5-) (· .65: 1.7: 60.0: 93.3: 95.0 98.3: 60.0: 98.3)

i-; ; ; ; -I -, - S

(Processed. _: 1.7: 1.7 * 1.7 * 1.7 1.7: 0: 0) (ton ^ guovikal-,:::::::) 20

Conclusion: At the doses used, the plastic film impregnated with Compound A showed a significant insect repellent effect.

e) Deadly and repellent effect of paper and plastic film on Sitophilus granarius

A bag of about 150 cm in volume made of Compound A-treated material was placed with 10 g of intact grain, sealed, and placed in a one-liter can in the dark, and insects were introduced into the free space of the can.

After 7 days, the repulsive effect (number of live individuals intruding into the bag + number of dead individuals in the intruder towers divided by the total number of individuals) and lethal effect (number of dead individuals intruding into the bag + total number of dead individuals intruding into the bag) and 10 661 09 were determined.

The effect on the offspring was also studied by finding the number of new adult individuals 8 weeks 5 after the insects had been isolated at the end of the experiment.

Comparative experiments were performed by bag treatment.

In the comparative experiment, the insects are able to invade the bag of 10 countries, and therefore, in the evaluation of the lethal effect, living individuals invaded into the bag have been counted in the control group. The treated bags have a repulsive effect that prevents insects from penetrating the bag.

15 The experiment was performed in triplicate for each series and dose.

The results of the experiments are summarized in the following table: 11 66109 -------: - j--) (: Doses ‘.Effect Effect« Effect after-)

Start; / r2); 7 acting expenses. 7 days: Adults: adults

i s a .the number of individuals- S

\; | (reF «Jsio) · lethal; rS 8 vllkon Talut.

) *. . effect: tua living death-) 5) | _5 ___: Lei ta_) S 325: 100: 98.7 * | ; -: - i; 1. . 130: 100: 100:) \ PLASTIC:) 10 f. , .. 65: 100: 90,0 1} Treated- ^ ...)) tön comparative- '- \ - 7 ---- j \) snowwater' '' 1 \} aali "- I 76.1 ] 0 '_ (f Paper: 60: 100: 95 * 7: 8: ¾) 15).... \ F 100 100 100 0: l »} (Processed-5_5_ · _ · _ ·) - 5 5 '·::) (lumateri- ·' '"·:) (aali:: 77,1: 0: U73: 15) 20 (_: _ I _: _ I_j_)

Conclusion: At the doses used, the paper and plastic film impregnated with Compound A showed a significant insect repellent effect.

Claims (13)

66109 Packaging or coating material containing an active ingredient for controlling insects and mites, characterized in that the active ingredient consists of at least one compound of the general formula (I) 10 Ϊ - £ - O - | HX = Y (I) 15 where Y is a group of formula (I) HC CH-, Y 20 \ / \ / z 'where Z is a group of formula X1 \ 25 ΓΗ- X2 where and represent a chlorine or bromine atom , or Z is a group of the formula X, v-r X5 X5 wherein X1, X4 and X1 represent a chlorine or bromine atom, wherein the group (IA) is in the cis or trans configuration and optically active, and that the configuration of the alcohol moiety of the compounds (I) is (S). 13 661 09 Material according to Claim 1, characterized in that the compound of general formula (I) is (1R cis) -2,2-dimethyl-3- (2,2-dibromovinyl) cyclopropane-1-carboxylic acid (S) ° 4-cyano-3-phenoxybenzyl ester. Material according to Claim 1 or 2, characterized in that it consists of paper. Material according to Claim 3, characterized in that it contains from 10 mg to 1 g of active substance per square meter. Material according to Claim 3 or 4, characterized in that it contains 500 mg of (1R cis) -2,2-dimethyl-3- (2,2-dibromovinyl) cyclopropane-1-carboxylic acid (S) cyano-3-phenoxybenzyl ester per 15 square meters. Material according to one of the preceding claims 3 to 5, characterized in that the impregnation of the paper with the active substance is carried out on both sides. Material according to Claim 1, characterized in that it consists of a plastic film. Material according to Claim 7, characterized in that it contains from 10 mg to 2 g of active ingredient per square meter. Material according to Claim 7 or 8, characterized in that it contains 10 mg to 1 g of (1R cis) -2,2-dimethyl-3- (2,2-dibromovinyl) cyclopropane-1-carboxylic acid (S) - cyano-3-phenoxy benzyl ester per square meter. Material according to one of Claims 7 to 9, characterized in that the impregnation of the plastic film with the active substance is carried out as a mass impregnation. 66109 1. A packing material or an intermediate material which is active for the purposes of insertion and 5 qualities, which means more than one of the types of material used in the formulation (I): O CN / f λ Y - C - O - C- / \ io A \ == /> —v 1 "O color Y is a group of groups with form (I) 15 H, CY 3") Z_V color Z is a group of forms 25 (X2) or Z is in a group with a form of <. and in alcoholic form of the configuration (S).