CH616563A5 - Pesticide containing a 5-phenylcarbamoylbarbituric acid as active ingredient - Google Patents

Description

The present invention relates to a pesticide containing a 5-phenyl-carbamoyl-barbituric acid as active component and its use for pest control.

The 5-phenyl-carbamoyl-barbituric acid contained in the agent according to the invention corresponds to the formula I.

CO-NH-R »

I I

(i)

R.

wherein either i) Rj and R2 each represent a hydrogen atom or a methyl group and

R3 represents a phenyl group; or ii) Rj and R2 simultaneously represent a hydrogen atom and R3 a p-chlorophenyl, p-methylphenyl or o-methylphenyl group and their tautomers.

The compounds of formula I, i.e. H. 5-phenylcarbamoyl barbituric acid; 5-phenylcarbamoyl-1-methyl-barbituric acid; 5-phenylcarbamoyl-1,3-dimethyl 1-barbituric acid; 5- (4-chlorophenyl) carbamoyl barbituric acid; 5- (4-methylphenyl) carbamoyl barbituric acid; and 5- (2-methylphenyl) carbamoyl barbituric acid are known [cf. «Acta. Pole. Pharm. » 24 (6), 647-649 (1967); «Diss. Pharm. Pharmacol. » 18 (1), 31-50 (1966); Japanese Patent No. 1408 / '64; and «Chem. Ber. » 98, 131-139 (1965) 1 and can be obtained by methods known per se, e.g. B. by a) an ester of formula II

C00R,

R.

VV0

À À

L il 2 0

(II)

with an aniline of formal III

R3-NH2

implements;

5 b) a compound of formula IV

(III)

vv °

E ^ A

1 II 2

with an isocyanate of formula V

R3-N = CO

(IV)

(V)

20 can react; or that c) a compound of formula IV above with an azide of formula VI

R3_CO-N3

(VI)

treated; where in formulas II to VI Rj to R3 have the meanings already given under formula I and R4 represents a C1-C4-alkyl group.

Processes (a) and (c) are preferably carried out at a reaction temperature between 100 and 200 ° C. and process (b) at a reaction temperature between 0 and 200 ° C. The reactions can be carried out at normal or elevated pressure, if appropriate in a solvent or diluent which is inert to the reactants and, if appropriate, in the presence of a base.

Suitable solvents or diluents for these reactions are e.g. B. ethers and ethereal compounds such as dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran: 40 amides such as N, N-di-alkylated carboxamides; aliphatic aromatic and halogenated hydrocarbons, in particular toluene, xylenes and chlorobenzene; Nitriles such as acetonitrile; DMSO and ketones such as acetone and methyl ethyl ketone.

Bases include, in particular, tertiary amines, such as tri-45 ethylamine, dimethylaniline, pyridine, picolines and lutidines, furthermore hydroxides, oxides, carbonates and bicarbonates of alkali and alkaline earth metals and alkali metal alcoholates such as, for. As potassium t, butylate and sodium methylate into consideration.

According to the present invention, it has now surprisingly been found that the compounds of the formula I contained in the composition according to the invention have an outstandingly good insecticidal activity. In particular, the compounds of formula I have a very favorable action against plant and animal-damaging insects and can 55 z. B. according to the invention for combating insects of the families: Acrididae, Blattidae, Gryllidae, Gryllotalpidae, Tetti-goniidae, Cimicidae, Pyrrhocoridae, Reduviidae, Aphididae, Dephacidae, Diaspididae, Pseudococcidae, Chrysomelidae, Brucha, Scidaidaididae, Cocidaidaididae , Curculionidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Galleridae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae, Trypetidae and Pucilidae can be used. But above all, the compounds of formula I are suitable for controlling ectoparasitic insects such as 65. B. Lucilia sericata and insects that are harmful in the areas of hygiene and conservation.

The insecticidal action of the agent according to the invention can be achieved by adding other insecticides and / or

3rd

616 563

Significantly widen acaricides and adapt them to the given circumstances.

As additives are such. B .: org. Phosphorus compounds; Nitrophenols and their derivatives; Formamidines; Ureas; pyrethrin-like compounds; Carbamates and chlorinated hydrocarbons.

To produce the agent according to the invention, the compounds of the formula I are mixed together with suitable carriers and / or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. B. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.

For the preparation of the agent, the compounds of formula 1 can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in conventional formulations which are common knowledge in application technology.

Agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding compounds of the formula I with the suitable excipients, if appropriate with the addition of dispersants or solvents which are inert to the active ingredients. The active ingredients can be present and used in the following processing forms:

Fixed processing forms:

Dusts, scattering agents and granules (coating granules, impregnation granules and homogeneous granules);

Liquid processing forms:

a) active ingredient concentrates dispersible in water: wettable powders, pastes and emulsions;

b) solutions.

The content of active ingredient (compound of formula I) in the agents described above is between 0.1 to 95%. The following examples serve to explain the invention in more detail.

Example 1 Production of Agents According to the Invention

A. Dusts:

The following substances are used to produce a) 5% and b) 2% dust:

a) 5 parts of active ingredient,

95 parts talc;

b) 2 parts of active ingredient,

1 part of highly disperse silica,

97 parts of talc.

The active ingredients are mixed and ground with the carriers.

B. Granules:

The following substances are used to produce 5% granules:

5 parts of active ingredient,

0.25 parts epichlorohydrin,

0.25 parts of cetyl polyglycol ether,

3.50 parts of polyethylene glycol,

91 parts of kaolin (grain size 0.3-0.8 mm). The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and the acetone is then evaporated in vacuo.

C. wettable powder:

To produce a) 40%, b) and c) 25%,

d) 10% wettable powder, the following components are used:

a) 40 parts of active ingredient,

5 parts of sodium lignosulfonic acid,

5 1 part of dibutylnaphthalenesulfonic acid sodium salt, 54 parts of silica;

b) 25 parts of active ingredient,

4.5 parts of calcium lignin sulfonate,

1.9 parts champagne chalk / hydroxyethyl cellulose lo mixture (1: 1),

1.5 parts of sodium dibutyl naphthalenesulfonate,

19.5 parts of silica,

19.5 parts of champagne chalk,

28.1 parts of kaolin;

15 c) 25 parts of active ingredient,

2.5 parts of isooctylphenoxy-polyethylene-ethanol,

1.7 parts champagne chalk / hydroxyethyl cellulose mixture (1: 1),

8.3 parts of sodium aluminum silicate,

20 16.5 parts of diatomaceous earth,

46 parts of kaolin;

d) 10 parts of active ingredient,

3 parts mixture of the sodium salts of saturated fatty alcohol sulfates,

25 5 parts naphthalenesulfonic acid / formaldehyde condensate, 82 parts kaolin.

The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. Spray powder is obtained which can be diluted with 30 water to form suspensions of the desired concentration.

D. Emulsifiable concentrates:

The following substances are used to produce a) 10% emulsifiable concentrate:

a) 10 parts of active ingredient,

3.4 parts of epoxidized vegetable oil,

3.4 parts of a combination emulsifier, consisting of fatty alcohol polyglycol ether and alkylarylsulfonate-40 calcium salt,

40 parts of dimethylformamide,

43.2 parts of xylene.

Such a concentrate can be used to prepare emulsions of the desired concentration by dilution with water.

E. Spray agent:

The following constituents are used to prepare a) 5% and b) 95% spray: 50 a) 5 parts of active ingredient,

1 part epichlorohydrin,

94 parts of gasoline (boiling limits 160-190 ° C);

b) 95 parts of active ingredient,

5 parts epichlorohydrin.

55

Example 2

Insecticidal feeding poison effect: Spodoptera littorälis Heliothis virescens and Leptinotarsa decemlineata Cotton plants and potato plants were sprayed with a 60 0.05% aqueous active ingredient emulsion (obtained from a 10% emulsifiable concentrate).

After the covering had dried on, the cotton plants were each populated with Spodoptera littoralis and Heliothis virescens larvae (L3 stage) and the potato plants with Leptino-65 tarsa decemlineata larvae (L3). The killings achieved were evaluated after 2, 4, 8, 24 and 48 hours. The test was carried out at 24 ° C and 60% relative humidity.

616 563

4th

In the above experiment, compounds of the formula I showed good feeding poison activity against Spodoptera littoralis, Heliothis virescens and Leptinotarsa decemlineata larvae.

Example 3 Action against Chilo suppressalis 6 rice seedlings of the Caloro variety were grown in plastic pots in such a way that their roots were matted into a disc. The roots were immersed in a 0.08% drug solution and drained. Then 5 test animals (Chilo suppressalis larvae in the L2 stage) were placed in a pot and the treated plants were placed on them.

A percentage evaluation of the mortality achieved was carried out after 5 days.

Compounds of formula 1 showed good activity against Chilo suppressalis in this test.

Example 4 Action against Lucilia sericata 2 ml of an aqueous solution containing 0.1% test substance are added to 2 ml of a culture medium. Now about 30 freshly hatched Lucilia sericata larvae are added to the culture medium and after 96 hours the insecticidal activity is determined by determining the kill rate. Compounds of the formula I showed good activity against Lucilia sericata larvae in the test above.

Example 5

Insecticidal contact effect: Aphis fabae One day before application, broad beans (Vicia faba) grown in pots were infected with about 200 aphids (Aphis fabae) per plant. The application was carried out by means of a compressed air syringe on the leaves covered with lice with a spray mixture in a concentration of 1000 ppm (made from a 25% wettable powder).

The ratings were given 24 hours after the application. Compounds of the formula I showed good contact activity against Aphis fabae in the above test.

Example 6

Antioxidant effect: Leptinotarsa decemlineata Two 15 cm high potato plants were sprayed with 25 ml of an acetone / water mixture (1: 1) containing 0.05% test substance.

After the topping had dried on, the potato plants were populated with 10 larvae of the species Leptinotarsa decemlineata (L3 stage). A plastic cylinder was then placed over the plant to prevent the larvae from migrating. A copper gauze lid served as the end. The feeding damage was determined after 2 days.

Compounds of the formula I showed a positive antiperspirant effect in the above experiment.

15 Example 7

Antioxidant effect: Spodoptera littoralis Two 15 cm high cotton plants were sprayed with 25 ml of a solution containing 0.1% test substance (acetone / water 1: 1). After drying, 20 5 larvae of the species Spodoptera littorales (L3 stage) were placed on each plant. A plastic cylinder was placed over the plant and sealed with a copper gauze cover. The feeding damage was determined after 2 days.

Compounds of the formula I showed a good antioxidant activity in the above experiment.

Example 8 Effect against Musca domestica 50 g of CSMA maggot substrate were weighed into beakers. From a 1% acetone solution, 2.5 ml per active substance were pipetted twice onto 50 g of maggot substrate. After the mixed substrate has been mixed, the solvent is allowed to evaporate. 25 1-, 2-, 3-day maggots and approx. 50 fly eggs were then put on each active ingredient. After the pupation was completed, the dolls were washed out and counted. After 10 days, the number of flies hatched was determined and any influence on the metamorphosis was determined.

Compounds of the formula I showed a good activity against Musca domestica in the above experiment.

Claims (2)

616 563 2nd PATENT CLAIMS 1. Insecticidal agent, containing as active component a compound of formula I. CO-NH-R " 0, I. tAA R1 j | 2 0 wherein either i) Rj and R2 each represent a hydrogen atom or a methyl group and R3 represents a phenyl group; or ii) R 1 and R 2 simultaneously represent a hydrogen atom and R 3 represents a p-chlorophenyl, p-methylphenyl or o-methylphenyl group, and their tautomers. 2. Use of an agent according to claim 1 for controlling insects.