CA2091064C

CA2091064C - Insecticidal composition

Info

Publication number: CA2091064C
Application number: CA002091064A
Authority: CA
Inventors: Franz Bencsits
Original assignee: Perycut-Chemie AG
Current assignee: Perycut-Chemie AG
Priority date: 1990-09-12
Filing date: 1991-09-12
Publication date: 2000-06-27
Anticipated expiration: 2011-09-12
Also published as: CZ284864B6; HU213036B; EP0548171B1; ES2095953T3; DE59108411D1; RU2097971C1; EP0548171A1; WO1992003926A1; CA2091064A1; HU9300694D0; GR3022015T3; DE9013000U1; HUT63943A; DK0548171T3; CZ36493A3; ATE146034T1

Abstract

The invention concerns an insecticidal composition containing at least one pyrethroid, at least one UV-absorbing agent and at least one anti-oxidant which may be a derivative of tocopherol or an ester of citric acid. This insecticidal composition can be used as an emulsion, or on a powder-form carrier, against flying and crawling insects such as flies and cockroaches.

Description

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INSECTICIDAL COMPOSITION
BACKGROUND OF THE INVENTION
The present invention relates to an insecticidal composition comprising an active amount of at least one pyrethroid, at least one W absorbing agent and at least one anti-oxidant, and its use for controlling flying and crawling insects.
The insecticidally effective components of pyrethrum and its synthetic analogues, which are derived from the structure indicated in the following, are designated as pyrethroids. The main active substances in pyrethrum are the cinerins I and II, the pyrethrins I and II and the jasmolins I and II (Rompps Chemie-Lexikon, 8th edition (1987), page 3413).
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Pyrethrin I: R1 = CH=CH2, R2 = CH3 Pyrethrin II: R1 = CH=CH2, R2 = COOCH3 Cinerin I: R1 = R2 = CH3 Cinerin II: R1 = CH3, R2 = COOCH3 Jasmolin I: R1 = C2H5, R2 = CH3 Jasmolin II: R1 = C2H5, R2 = COOCH3 Allethrin: R1 = H, R2 = CH3 w i.l ~ .~. '~ ~ ~~
~i E,.:.l Pyrethrum is obtained from the dried flower heads of various pyrethrum or chrysanthemum species by pulver-ization or extraction and contains as main active substances pyrethroids such as pyrethrins, cinerins and jasmolins. Apart from nicotine, pyrethrum is the strongest vegetable insecticide; however, its effec-tiveness is reduced by sunlight and heat (Rcimpps Chemie-Lexikon, 8th: edition (1987), page 3414). The lack of stability, but also the high price of natural .
pyrethroids led to the development of numerous syn-thetic derivatives.
Pyrethroids are generally used as isomer mixtures. They have been used for a long time as insecticides, in , particular against common houseflies, cockroaches or blackbeetles and other household vermin, moths, corn weevils, mosquitoes, garden and greenhouse parasites, hay worms in viticulture and boll-weevils. Particular-ly, the natural pyrethroids distinguish themselves by a rapid so-called knock-down effect, i.e. the insects are certainly paralyzed rapidly, but only temporarily, and they recover again. The oxidative detoxication meta-bolism of the insects is responsible for this undesired effect.
Due to the great instability of the pyrethroids to air and light, numerous attempts have already been made to stabilize pyrethroids and to prolong their effective-ness.
Pyrethrum Post 11(4), 135-7, 51 and J. Agr. food Chem, 20(2), 313-15 disclose the stabilizing of pyrethrins and allethrin by the additian of an antioxidant~and a Uv absorbing agent in a mineral oil formulation. While non-stabilized formulations are destroyed almost ~ ~,,~ ~ :.; ! ~ i ~ ~ !y- ~ ~-~ c ~~

completely within 4 hours, the combination of an oxidant and a UV absorbing agent results in a consider-able stabilization of the pyrethroids for at least 4 hours and more.
Aromatic ketones in which two aromatic rings are directly bonded to an oxo group, e~g~ benzophenone derivatives, and esters of aromatic acids, such as esters of substituted benzoic acids are mentioned. The used antioxidants have an OH group, which is directly bonded to an aromatic ring, and at least 14 carbon atoms such as 4-methyl-2,6-di-tert.-butyl phenol or 2,6-dioctadecyl-p-cresol.
US-A-3 606 613, WO-A-86/03374, EP-A-147 947, DE-A-2 615 646 and GB-A-2 058 569 describe various insecticidal compositions on pyrethroid basis, which contain anti-oxidants and customary Uv absorbing agents for stabi-lizing the pyrethroids. 2,6-di-tert.-butyl-4-methyl phenol, 2,6-dioctade~yl-p-cresol, butylated hydroXy toluene, alkylated phenols, tert.-butyl hydroquinone, butylated hydroxy anisoles, ethoxy , ascorbic acid, their salts and derivatives and propionic acid salts are used as antioxidants. However, the stability of these compositions is not satisfactory.
It is the object of the present invention to provide an insecticidal composition with improved long-term effect.
SUN~1ARY OF THE INVENTION
This object is solved by an insecticidal composition of the type mentioned at the beginning, which is char-acterized in that the contained antioxidant is at least one citric acid ester.

BRIEF DESCRIPTION OF THE DRAWING
Figure 1 is a plot of peroxide numbers and conductivities for various insecticide compositions versus time.
DETAILED DESCRIPTION OF THE INVENTION
The composition according to the invention is suited for the control of vermin such as household vermin, in particular flies and cockroaches or blackbeetles.
The insecticidal composition has surprisingly a greatly improved long-term effect against vermin due to its high stability to W light and/or its resistance to oxidation. The sensistivity of the composition to W
light is attributable to an oxidation of the free fatty acids, an autoxidation by a chemical reaction of air oxygen with the double bonds contained-in unsaturated fatty acids being also possible. This sensitivity is drastically reduced according to the invention by the use of citric acid esters as an antioxidant. Ascorbyl palmitate may be contained as a further antioxidant.
The citric acid esters are preferably mono- to tri-esters of citric acid with alkyl alcohols having 1 to 8 carbon atoms.
The antioxidant is used in the composition used accord-ing to the invention preferably in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.03% by weight, based on the composition.
All natural and synthetic pyrethroids, either alone or in mixture, can be used in the insecticidal composition 4a used according to the invention. Natural pyrethrum proved to be especially effective.
The pyrethroid is preferably used in an amount of 0.001 to 10~ by weight, especially preferred of 0.01 to 2% by weight, in particular of 0.03% by weight, based on the composition.

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W absorbing agents used according to the invention are generally known. Especially suited W absorbing agents, which are effective in the wave length range of 250 to 350 nm, which is of interest here, are benzoic acid derivatives, e.g. p-amino benzoic acid derivatives such as amyl-p-dimethyl amino benzoate and glyceryl-p-amino benzoate or o-hydroxy benzoic acid derivatives; benzo-phenone derivatives, e.g. 2-hydroxy-4-(2-hydroxy-3-methacryloxy) propoxy benzophenone or 2-hydroxy-4-meth- .
oxy benzophenone-5-sulfonic acid; camphor derivatives, coumarin derivatives, benzimidazole derivativs; diben-zoyl methane derivatives; cinnamic acid ester derivat-ives, e.g. isobutyl cinnamate, ethyl cinnamate or benzyl cinnamate; and Iris-(hydroxy methyl) amino-methane salts of a sulfonic acid such as tris-(hydroxy methyl) aminomethane salt of 2-phenyl benzimidazole-5-sulfonic acid. ._ The W absorbing agent is preferably used in an amount of 0.001 to 10% by weight, especially preferred of 0.01 to 5% by weight, in particular of 0.030 by weight, based on the composition.
The insecticidal composition used according to the invention is suitably produced in liquid form with the addition of a diluent or solvent. Suited diluents are water, organic solvents or oils, an aqueous and/or oily emulsion being preferred. Monohydric and polyhydric alcohols, glycols such as 1,2-propane diol, and halo-genated hydrocarbons can e.g. be used as organic diluents, while saturated and unsaturated ceric acid esters and fatty acid esters, e.g. vegetable oils, and natural and synthetic ethereal oils are especially well suited as oils. In addition, the insecticidal composit-ion may contain lecithin. In practical application, the 1_ ~~ "
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insecticidal composition can then be sprayed onto the surface to be treated.
The preparation of the insecticidal composition in powder form is carried out in customary fashion by adding a solid carrier such as talcum, zinc and titan-ium dioxide, calcined magnesia or an anhydrous metal salt.
The insecticidal composition according to the invention can be used against any type of vermin, against which the already known pyrethroid compositions are used, in particular to destroy household vermin such as flies and cockroaches.
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Claims

1. An insecticidal composition comprising an effective amount of at least one pyrethroid, of at least one UV
absorbing agent and at least one antioxidant, characterized in that the antioxidant is at least one citric acid ester.

2. A composition according to claim 1, characterized in that the pyrethroid is pyrethrum.

3. A composition according to claim 1 or 2, characterized in that the UV absorbing agent is a benzoic acid derivative, a benzophenone derivative, a benzoxazole derivative, a camphor derivative, a coumarin derivative, a benzimidazole derivative, a dibenzoyl methane derivative, a cinnamic acid ester derivative or a tris-(hydroxy methyl) aminomethane silt of a 5-sulfonic acid.

4. A composition according to any of claims 1 to 3, characterized in that the UV absorbing agent is a p-aminobenzoic acid derivative.

5. A composition according to any of claims 1 to 4, characterized in that it contains 0.001 to l0% by weight of the pyrethroid.

6. A composition according to claim 5, characterized in that it contains 0.01 to 2% by weight of the pyrethroid.

7. A composition according to any of claims 1 to 6, characterized in that it contains 0.001 to 10% by weight of the UV absorbing agent.

8. A composition according to claim 7, characterized in that it contains 0.01 to 5% by weight of the UV
absorbing agent.

9. A composition according to any of claims 1 to 8, characterized in that it contains 0.001 to 10% by weight of the antioxidant.

10. A composition according to claim 9, characterized in that it contains 0.01 to 5% by weight of the antioxidant.

11. A composition according to any of claims 1 to 10, characterized in that it contains ascorbyl palmitate as a further antioxidant.

12. A composition according to any of claims 1 to 11, characterized in that it contains customary carriers and/or diluents.

13. A composition according to claim 12, characterized in that it is present in aqueous and/or oily emulsion.

14. A composition according to any of claims 1 to 13, characterized in that it contains additionally lecithin.

15. Use of the insecticidal composition according to any of claims 1 to 14 for controlling flying and crawling insects, in particular flies and cockroaches.