NO832456L - Insecticide-PREPARATIONS - Google Patents

Description

The present invention relates to new pyrethroid-like insecticide preparations. The new preparations are particularly distinguished by their strong adhesion and long duration of action.

The pyrethroid has gained great importance in recent times due to the high and rapid interserticidal effect and low toxicity for humans and animals. The natural and the synthetic pyrethroids are poorly water soluble, heat sensitive and are easily inactivated in air. In addition to this, the pyrethroids are very expensive products because the complicated isolation (natural pyrethroids) or complicated syntheses.

The aim of the present invention is therefore to provide new insecticide preparations which contain pyrethroids as active active substances and which, with a small amount of active substance, show a good and long-lasting effect and good adhesion to what is to be protected.

It has now been surprisingly found that very effective preparations for combating harmful insects can be obtained when the pyrethroids are used together with a phospholipid from the group of phosphatidylcholine, phosphatidylethanolamine or N-acylphosphatidylethanolamine or a mixture of several such phospholipids in a weight ratio of 1:20 to 1:50 alongside usual carriers, diluents, dissolvers, sprays and/or other inert aids.

By adding phospholipids, a significantly better distribution and better adhesion is achieved and thus also a longer working time. Thereby, the amount of active substance can be reduced considerably (up to 60%).

A good distribution is of great importance, as for spraying in the field, e.g. of cotton or tobacco fields, only 25 - 70 grams of active substance per hectares of the usual<p>repairs. With the new preparations, effective amounts of 10-60 grams per hectares without thereby affecting the effect.

The new preparations are also suitable for the treatment of ecto-parasites in domestic and farm animals. They show a good adhesion to the animal's skin or hair coat. When spraying stable walls, the active substance adheres well to the wall and provides long-lasting protection against insects such as flies.

As phospholipids, natural or synthetic phospholipids from the group of phosphatidylcholine, hydrogenated phosphatidylcholines, phosphatidylethanolamine, N-acylphosphatidylethanolamines, phorfatidylinositol, phosphatidylglycerol or a mixture of several such phospholipids come into consideration, especially mixtures of phosphatidylcholine and phosphatidylethanolamine or phosphatidylcholine with phosphatidylethanolamine and N-acylphosphatidylcholine. -dylethanolamine or other phosphatidyl mixtures with 15-75% phosphatidylcholine.

Particularly preferred are natural phosphatidylcholines which can be produced by methods described in the following patents: DE-PS 10 47 579, DE-PS 10 53 299, DE-PS 16 17 679, DE-PS 16 17 680, DE-OS 30 47 048 , DE-OS 30 47 012,

DE-OS 30 37 011.

Natural or synthetic pyrethroids of the general formula I come into consideration as pyrethroids

where R = CH3, COOH, CO0CH3, Cl, Br

R2= CH3, Cl, Br, Aryl, Halogen, subst. Aryl

R., = subst, cyclopentene, subst, furylmethyl, :phthalimidomethyl, phenoxybenzyl or phenalkenyl groups.

Examples with formula I:

The compounds of formula I are known compounds which have already proved beneficial as insecticides ("Chemie der Pflanzenschutz- und Schådlingsbekåmp-fungsmittel1; Springer 1970, p. 87 ff).

For the production of the new insecticide preparations, the corresponding phospholipid is dissolved in a suitable solvent such as e.g. toluene, acetic acid esters, xylene, petrol, methanol or ethanol or mixtures thereof. The choice of solvent depends on the dissolution properties of the active substance used. In the phospholipid solution, the active substance or a commercially available formulation is optionally dissolved during heating. After completion of the dissolution process, the solvent is distilled off in a vacuum while heating. The product thus obtained is then possibly processed with the addition of suitable inert aids such as fillers, swelling agents, emulsifiers, wetting agents, spraying aids etc. to normal commercial products.

The new insecticide preparations can also be prepared by dissolving the active substance or a commercially available preparation, phospholipid and further desired auxiliaries together in the solvent or solvent mixture by heating or suspending them, and that the solvent or mixture thereof is then drawn off under vacuum. A finished mixture is obtained that can be used immediately.

In the case of active substances that are soluble in water or a water-alcohol mixture, the active substance is preferably first dissolved in water or the water-alcohol mixture and the phospholipid or the phospholipid mixture is then processed into a solution or emulsion under stirring or using ultrasound. The possibly necessary emulsifiers can be added before or after this stirring process. The emulsions or solutions thus obtained are then liberated in the usual way, e.g. by distillation, spray drying, lyophilization, freed from the solvent mixture or water. The resulting product can be used as a dry product, possibly with the addition of auxiliaries and fillers. Furthermore, the product can be emulsified or dissolved again, during use

of proprietary excipients and then used as a liquid product.

Emulsion concentrates are preferably prepared by dissolving phospholipid in the presence of co-emulsifiers in a solvent or a solvent mixture and pyrethrin is added with stirring and slight heating. The obtained concentrate can be processed before use by adding the required amount of water to ordinary spray compounds.

Carrier materials are e.g. talc, kaolin, bentonite, silicon dioxide, lime and stone flour. Additional aids are e.g. surface-active compounds such as soaps (fatty acid salts), fatty alcohol sulphonates or alkyl sulphonates. Gelatin, casein, albumin, starch or methylcellulose can be used as stabilizers or protective colloids. You can also use agents such as silicone oil, fatty acid esters, triglycerides, fatty alcohol or fatty acids.

As common synergists for pyrethroids, e.g. piperonyl butoxide, safroxan, sesamex or sesamin.

The new preparations can be used as sprays, solutions, emulsions or suspensions.

Example 1.

2,000 g of pyrethrum extract from the company INEXA, Quito-Ecuador

Lot 1041 (Pyrethrin content approx. 59.3%)

2.105 g phospholipid

1,595 g of isophorone

0.800 g glycerin

0.26 5 g cremophor EL

0.235 g of methanol

The phospholipid is dissolved in the mixture of isophorone, glycerine, cremophor and methanol with stirring and then put pyr-

the ether extract to this solution with stirring and

light heating.

Analogous to example 1, the following mixtures are prepared:

Example 2.

0.40 g permethin

3.00 g piperonyl butoxide

2.00 g phospholipid

1.75 g isophorone

0.75 g glycerin

0.2 5 g cremophor EL

0.25 g of N-(2-hydroxyethyl)-caproic acid amide

Example 3.

1.70 g of cypermethrin

1.70 g of piperonyl butoxide

2.00 g phospholipid

1.75 g isophorone

0.75 g glycerin 0.2 5 g cremophor EL

0.26 g softigen 767

Example 4.

0.90 g decamethrin

2.50 g of piperonyl butoxide

2.00 g phospholipid

1.75 g isophorone

0.75 g glycerin

0.25 g cremophor EL

0.25 g softigen 767

Example 5.

0.20 g permethrin

3.20 g piperonyl butoxide

1.66 g phospholipid

0.83 g cremophor EL

0.065 g triethylamine

1.17 g of toluene

1.17 g xylene

0.6 25 g DMSO

0.33 g vegetable oil

0.83 g of N-(2-hydroxyethyl)-caproic acid amide

Example 6.

1.70 g permethrin

1.70 g of piperonyl butoxide

1.66 g phorfolipid

1.66 g of isophorone

0.83 g cremophor EL

0.83 g of N-(2-hydroxyethyl)-caproic acid amide

2.15 g of DMSO

0.63 g glycerin

0.18 g of methanol

0.33 g vegetable oil

The phospholipid products used in the above-mentioned examples 1-6 had the following composition, whereby the indicated percentages are weight percentages and the abbreviations used have the following meaning:

pc = phosphatidylcholine

pe phosphatidylethanolamine

ape = n-acylphosphatidylethanolamine

pl = other phospholipids

pi = phosphatidylinositol

b = example

bl: 40% pc, 28% pe, 27% ape, 5% pl

b2: 45% pc, 25% pe, 21% ape, 9% pl

b3: 42% pc, 25% pe, 25% ape, 8% pl

b4: 40% pc, 30% pe, 25% ape, 5% pl

b5: 96% pc, 4% pl

b6: 30% pc, 16% ape, 24% pe, 30% pl

Claims (11)

1. Insecticide preparation, characterized in that it consists of a) an insecticidally active substance from the group of pyrethroids, and b) one or more phospholipids from the group phosphatidylcholine hydrogenated phosphatidylcholines, phosphatidylethanolamine, N-acyl-phosphatidylethanolamines, phosphatidylinositol, phosphatidylserine, lysolecithin and phosphatidylglycerol, in the weight ratio a : b of 1 : 20 to 1 : 50, alongside usual carriers, diluents, solvents, dispersing aids and other inert aids. 2. Preparation according to claim 1, characterized in that as phospholipid it contains mixtures of phosphatidylcholine and phosphatidylethanolamine or mixtures of phosphatidylcholine, phosphatidylethanolamine and N-acyl-phosphatidylethanolamine. 3. Preparation according to claims 1 and 2, characterized in that it contains as phospholipid a phospholipid with a content of 15 - 75% phosphatidylcholine. 4. Preparation according to claims 1-3, characterized in that the pyrethroid contains a compound with the general formula in which R± = CH 3 , COOH, COOCH 3 , Cl, Br R2 = CH3 , CL, Br, Aryl, Halogen subst. Aryl R3 = subst, cyclopentene, subst, furylmethyl, phthalimidomethyl, phenoxybenzyl or phenalkenyl groups. 5. Preparation according to claims 1-4, characterized in that the pyrethroid contains permethrin, decamethrin or cypermethrin. 6. Use of preparations according to any one of claims 1-5, for insect control. 7. Process for the production of preparations according to any one of claims 1-5, characterized in that the phospholipid is dissolved in an organic solvent or a mixture thereof and that the active substance is dissolved in this solution, possibly under heating and/or stirring, and that the solvent or the mixture thereof is then drawn off in a vacuum and the mixture thus obtained is transferred by the addition of usual fillers and auxiliaries to a usual application form. 8. Process for the production of preparations according to any one of claims 1-5, characterized in that the active substance(s) together with one or more phospholipids, possibly adding common fillers or auxiliaries, are dissolved in an organic solvent respectively are slurried therein and that the solvent is then drawn off. 9. Method for producing preparations according to any one of claims 1-5, characterized in that one or more water- or alcohol-soluble active substances are dissolved in water or water-alcohol mixtures together with one or more phospholipids while stirring and /or light heating and/or ultrasound and that the solvent or the solvent mixture is drawn off. 10. Method for producing preparations as an emulsion concentrate according to any one of claims 1-5, characterized in that the phospholipid is dissolved in the presence of an emulsifier in an organic solvent or a mixture of such, and that the active substance dissolves dissolve in this solution, possibly during heating and/or stirring. 11. Use of emulsion concentrates according to claim 10, for combating insects, characterized in that the concentrate is diluted with water and used as a spray compound.