DE2719777A1 - NEW 5-PHENYL CARBAMOYL BARBITURIC ACIDS - Google Patents

Description

Dr. F. Zumstein Sr. - Dr. E. Assmann - Or R. Koenigsberger Dipl.-Phys. R. Holzbauer - ») ipl .- 'rg. F. Kltngseisen - Dr. F. Zumstein jun.

PATEN IANI / VÄLVE

TELEPHONE: COLLECTING NO. 22 53 41

TELEX 529979

TELEGRAMS: ZUMPAT CHECK ACCOUNT: MUNICH 91139-809. BLZ 700100 SO BANK ACCOUNT. BANK H. HOUSES

ACCOUNT NO. 397997, bank code 70030600

-Ä-

β MUNICH 2.

BRAUHAUSSTRASSE 4

Case 5-

CIBA-GEIGY AG, CH-4002 Basel / Switzerland

NEW S-PHEKYLCARBAMOYL BARBITURIC ACID

The present invention relates to new 5-phenylcarbamoyl-barbituric acids which have an action against insects, processes for their preparation and insecticidal compositions which contain this acid as an active component and processes for controlling insects using the new compounds.

The new 5-phenylcarbamoylbarbituric acids according to the invention correspond to formula I.

0 — NU — R,

(D

wherein

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CIBA-GEIGY AG

R, a methyl or ethyl group and R "denote a Cj-C.-alkyl or allyl group and R_ fllr a substituted phenyl group of the formula

R / is a halogen atom or a methyl or

Trifluoromethyl group and Rc is a hydrogen or halogen atom or a

Methyl- Oiler Tri Π normet liyl p.rnppe represent, stands.

The term "halogen" means chlorine, fluorine, bromine and iodine. The methyl, ethyl, n-propyl, isopropyl, η-butyl, isobutyl, sec-butyl and tert-butyl groups come into consideration as C _{1 -C -alkyl groups.}

Of particular importance because of their action against insects, especially those that are harmful to plants and animals Insects, are the compounds of the formula I in which R # is a chlorine, bromine or iodine atom or a

Trifluoromethyl group and Rt is a hydrogen, chlorine, bromine or iodine atom or a Mean methyl or trifluoromethyl group,

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TMl ΠΜ

CIBA-GEIGY AG

wherein the compounds of formula I wherein

R »for a 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethylphenyl-, 4-trifluoromethylphenyl-, 3,5-bis-trifluoromethylphenyl-, 3-chloro-4-trifluoromethylphenyl-, 4-chloro-3-trifluoromethylphenyl or 4-chloro-2-methylphenyl group.

develop a particularly good insecticidal effectiveness.

The compounds according to the invention, in which

i) R ~ is a methyl, ethyl or isopropyl group and ii) R _{2 is} an isobutyl or allyl group.

The compounds of formula] are obtained by methods known per se by e.g. a) an ester of the formula II

(II)

with an aniline of the formula III

tau Ϊ TTT ^

implements :;

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b) a compound of the formula IV

with an isocyanate of the formula V

R, H = CO (V)

lets react; or that one

c) a compound of the above formula IV with an azide of the formula VI

(VI)

treated, where in the formulas II to VI R ^. to R ^ have the meanings already given under formula I and R ^ is a CL-C ^ -alkyl group.

Preferably, v / ground the method (a) and (c) carried out at a reaction temperature between 100 and 200 ⁰ C and the method (b) at a reaction temperature between 0 and 200 ⁰ C. The reactions can be carried out at normal or elevated pressure, if appropriate in a solvent or diluent which is inert towards the reaction components, and if appropriate in the presence of a base.

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A "

As a solvent or diluent for these reactions e.g. ether and ether-like compounds are suitable, such as Dipropyl ether, dioxane, dimethoxyethane and tetrahydrofuran * Amides such as N, N-di-alkylated carboxamides; aliphatic aromatic and halogenated hydrocarbons, in particular Toluene, xylenes and chlorobenzene; Nitriles like

Acetonitrile; DMSO and ketones such as acetone and methyl ethyl ketone.

The bases are in particular tertiary amines, such as triethylamine, Dimethylaniline, pyridine, picolines and lutidines, also hydroxides, oxides, carbonates and bicarbonates of alkali and Alkaline earth metals and alkali metal alcoholates such as potassium t, butylate and sodium methylate are considered.

The starting materials of the formulas II to VI are known (see e.g. "Chem. Ber." 54, 1038 [1921]) or can be used analogously to known compounds are established.

The compounds according to the invention are in various tautomeric (keto / enol) forms.

The term of the invention is to be understood as meaning the individual tautomers and their mixtures.

According to the present invention, it has now surprisingly been found that the compounds of the formula I are advantageous

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- St »-

Effect against insects, in particular against insects that at Cause damage to plants and animals. For example, these substances work against eggs, larvae, nymphs, Pupae or adults of insects of the families:

/ "Anobiidae, Bostrichidae, Bruchidae, Chrysomelidae,

order
Colleoptera

order
Diptera

Cleridae, Curculionidae, Dermestidae, Elateridae, Ipidae, Lathridiidae, Nitidulidae, Ptinidae, Cucujidae, Scarabaeidae and Tenebrionidae;

Agromycidae, Anthomyiidae, Calliphoridae, Cecidomyiidae, Chloropidae, Gastrophilidae, Hippoboscidae, Hypodermidae, Muscidae, Stomoxydae,

Tabanidae, Tipulidae and Trypetidae; as well as the families: Noctuidae and Pyralidae (order Lepidoptera).

But above all, the compounds of formula 1 are suitable for Control of plant-damaging insects of the order Colleopter; in particular of the families Chrysomelidae and Curculionidae (e.g. Leptinotarsa decemlineata and Anthonomus grandis) as well as for Control of ectoparasitic insects of the Calliphoridae family, especially the genus Lucilia (such as Lucilia sericata). The use of the compounds according to the invention for the treatment of cotton and fruit crops as well as for external use is accordingly To emphasize the treatment of farm animals or the treatment of their environment.

The insecticidal action of the compounds according to the invention can by the addition of other pest control agents (e.g. insecticides and acaricides) widen considerably Adjust circumstances.

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Examples of suitable additives are: organic phosphorus compounds; Nitrophenols and their derivatives; Formamidine; Ureas; pyrethrin-like compounds; Carbamates and chlorinated Hydrocarbons.

The compounds of formula I can be used alone or together with suitable supports and / or aggregates can be used. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology, such as natural or regenerated Substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.

For application, the compounds of the formula I can be added to dusts, emulsion concentrates, granules, dispersions, Sprays, to solutions or to muddy in usual Formulations that are part of general knowledge in application technology can be processed.

The agents according to the invention are produced in an in a known manner by intimately mixing and / or grinding compounds of the formula I with the appropriate ones Carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients.

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In this context it should be mentioned that the active compounds of formula I, some of which as such in aqueous Media are sparingly soluble in the formulation of the invention Agents can also be used in the form of their size with bases (e.g. as triethylamine salts). Such salts that can be easily produced by customary methods, have an increased solubility and are accordingly in the production to recommend certain forms of use.

The compounds (active ingredients) of the formula I can be used in the following Forms of processing are available and used:

Forms of processing: dust, grit and

Granules (coating granules, impregnation granules and Homogeneous granules);

Liquid

Forms of processing:

a) dispersible in water

Active ingredient concentrates: wettable powder,

Pastes and emulsions;

b) Solutions

The content of active ingredient in the agents described above is between 0.1 and 95%, it should be mentioned that with the application from the aircraft or by means of other suitable application devices also higher concentrations can be used.

The active ingredients of the formula I can, for example, be formulated as follows:

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Sweeteners : To produce a) 5% and b) 2% dust, the following substances are used:

a) 5 parts of active ingredient,
95 parts of talc;

b) 2 parts of active ingredient,

1 part of highly disperse silica, 97 parts of talc.

The active ingredients are mixed with the carriers and marry.

Granules: The following substances are used to produce 5% granules:
5 parts active ingredient,
0, ^ S parts ep.ichl.orhydr.in,
0.25 parts of cetyl polyglycol ether, 3.5O parts of polyethylene glycol,
91 parts of kaolin (grain size 0.3-0.8 now).

The active ingredient is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and then the acetone is evaporated in vacuo.
Spray powder: For the production of a) 4O3igen, b) and c)

25% igpn and d) 10% wettable powder are the following ingredients Ic verv / ends:

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a) 40 parts of active ingredient,

5 parts of lignin sulfonic acid sodium salt, 1 part dibutylnaphthalenesulfonic acid sodium salt, Parts of silica;

b) 25 parts of active ingredient,

4.5 parts calcium lignosulfonate,

1.9 parts of Chaunpagne chalk / hydroxyethyl cellulose mixture (1: 1),

1.5 parts of liatrium dibutyl naphthalene sulfonate, 19.5 parts of silica, 19.5 parts of Champagne chalk, 28.1 parts of kaolin;

c) 25 parts of active ingredient,

2.5 parts of isooctylphenoxy-polyethylene-ethanol, 1.7 parts champagne chalk / hydroxyethyl cellulose

Gemiscii (1: 1), 8.3 parts of sodium aluminum silicate,

16.5 parts of kieselguhr, parts of kaolin;

d) 10 parts of active ingredient,

3 parts mixture of the sodium salts of saturated

Fatty alcohol sulfates, 5 parts of ilaphthalenesulfonic acid / formaldehyde condensate,
Share kaolin.

The active ingredients are mixed with the additives in suitable mixers intimately mixed and ground on appropriate mills and rollers. You get wettable powder, which with water to form suspensions of the desired concentration

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let it dilute.

Emulsifiable concentrates : The following substances are used to produce a) 10% and b) 25% emulsifiable concentrate:

a) 10 parts of active ingredient,

3.4 parts epoxidized vegetable oil,

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

40 parts of dimethylformamide and 43.2 parts of xylene;

b) 25 parts of active ingredient or its triethylamine salt,

2.5 parts epoxidized vegetable oil,

IO parts of a Λ1kylnrylsulfount / Fettalkoholpnly-

glycol ether mixture,
5 parts of dimethylformamide and 57.5 parts of xylene.

Such concentrates can be diluted with water to produce emulsions of the desired concentration. Spray : The following ingredients are used to produce a 5 / Ugen spray: a) 5 parts of active ingredient,

1 part epichlorohydrin,
94 parts of gasoline (boiling limits 160-190 ° C). .

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CIBA GEIGY AG. ^

The following examples serve to provide a more detailed explanation the invention.

example 1

Production of 5- (6-chlorophenyl) -carbamoyl-1,3-dimethyl- -barbitursclure.

To a solution of 15.6 g of 1,3-dimethylbarbituric acid in 15 (> ml of diethyl sulfoxide, 10.1 g of triethylamine and then 15.6 g in little Dimethylsul dissolved 4-chlorophenyl isocyanate foxyd added dropwise. one rllhrte the resultant reaction mixture for an additional 24 hours at Kmiinl iMiipiT.'it. ui "and gosi) the Heakt I onsmi" cliung then a solution of 15 ml of conc. Salzsüure in 350 ml The resulting condensation product:

was suction filtered and crystallized from dioxane. The compound of the formula was obtained

CO-NH

0 _xN / K 0

(Compound No. 1) N N

γ 0

with a m.p. of 225-227 ° C.

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CIBA-GEIGY AG

The following compounds of formula Ia are analogous to Way available

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Verb.
No. ^R l R ₂ ^R 4 * 5 M.p. C ° C) 2 CH ₃ CH ₃ 2-Cl 4-Cl 208-210 3 CH ₃ CH ₃ 3-CF ₃ 4-Cl 180-182 4th CH ₃ CH ₃ 4-CF ₃ H 188-190 5 CH ₃ CH ₃ 3-CF ₃ H 139-141 6th CH ₃ CH ₃ 3-CF ₃ 5-CF ₃ 184-185 7th CH ₃ CH ₃ 4-Br H 243-245 8th CH ₃ CH ₃ 4-y H 254-255 9 CH ₃ CH ₃ 4-F H 188-190 10 CH ₃ CH ₃ 3-Cl 4-Cl 205-206 11 CH ₃ CH ₃ 4-Cl 2-CH ₃ 179-180 12th CH ₃ CH ₃ 2-Cl 5-CF ₃ 212-213 13th CH ₃ CH ₃ 3-Cl 4-CF ₃ 160-161 14th CH ₃ CH ₃ CU ₃ H 176-179 15th CH ₃ C ₂ H ₅ 3-CF ₃ 4-Cl 124-126 16 CH ₃ C ₂ H ₅ 4-Br H 193-195 17th CH ₃ C ₂ H ₅ 2-Cl 4-Cl 133-135 18th CH C ₂ H ₅ 3-CF ₃ H 116-118 19th CH ₃ Ci) -C ₃ H ₇ 4-Cl H 183-185 20th CH ₃ (DC ₃ H ₇ 2-Cl 4-Cl 163-166

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Verb.
No. ^R l R ₂ ^R 4 «5 H M.p. (° C) 21 CH ₃ U) -C ₃ Il ₇ 4-Br H 183-185 22nd CH (DC ₄ II ₉ 4-Br 4-Cl 156-157 23 CH ₃ Ci) -C ₄ II ₉ 2-Cl H 157-158 24 CH ₃ (I) -C ₄ H ₉ 3-CF ₃ H 100-102 25th CH ₃ U) -C ₄ H ₉ 4-CF ₃ H 115-117 26th CH ₃ ! IH ₂ = CH-CH ₂ - 4-Br 4-Cl 124-125 27 CH ₃ ^ = CH-CH ₂ - 2-Cl H 143-145 28 CH ₃ ^ H ₂ = CH-CB ₂ - 3-CF ₃ '11 106-108 29 CIl ₃ JH ^ aI-CIi ₂ - 4- CF ₃ H 109-111 30th C ₂ H ₅ CjHj 4-Cl 4-Cl 164-166 31 C ₂ H ₅ C ₂ II ₅ 2-Cl H 143-144 32 C ₂ H ₅ C ₂ H ₅ 4-Br H 170-172 33 C ₂ H ₅ CjHj 4-CF ₃ 5-CP ₃ 34 C ₂ H ₅ CjHj 3-CF ₃

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Example 2 2719777

Insecticidal food poison effect: Leptinotarsa decemlineata Potato plants were made with a 0.05% aqueous emulsion the compound to be tested (obtained from a 10% emulsifier

concentrate) and, after the Leptinotarsa decemlineata larvae colonized in the L3 stage. Kan used two plants per test substance

and the evaluation of the destruction achieved was carried out 2, 4, 8, 24 and 48 hours after the start of the experiment. The experiment was carried out at 24 C and 607 relative humidity carried out.

The compounds according to Example 1 showed in the above experiment

a positive food poison effect against larvae of the species Leptinotarsa decemlineata.

Example 3

Insecticidal food poison effect: Spodoptera littoralis'

With the same working method using cotton plants and larvae of the species Spodoptera littoralis (L3) instead of potato plants and Leptinotarsa decemlineata The Vercuchs method described in Example 2 was repeated for larvae.

In this experiment, compounds 3, 5, 6 and a good effect against Spodoptera littoralis larvae.

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Example 4-

Insecticidal food poison / contact effect: Anthonomus grandis

Potted cotton plants were sprayed with a spray mixture containing 500 ppm, test substance (obtained from a 25% wettable powder) and allowed to dry off. Subsequently, the plants were populated with 5 one-day of the species Anthonomus grandis and kept the plants in greenhouse compartments at 24 ⁰ C and 60% relative humidity.

The number of dead or moribund insects was measured at intervals of 2, 4, 24 and 4-8 hours after the start of the experiment determined. Two plants were used per test substance.

In this experiment in particular, compounds according to Example 1 showed a very good action against Anthonomus grandis.

Example 5

Effect against Chilo suppressalis

6 ice seedlings of the Caloro variety were grown in plastic pots in such a way that their roots were matted to form a disc. The roots were immersed in a 0.08% solution of the compound to be tested and allowed to drain. Then 5 test animals (Chilo suppressalis larvae in the L ₂ stage) were each placed in a pot and the treated plants were placed on top.

Carried out an evaluation of the mortality rate achieved after 5 days and the test was carried out at 24 ⁰ C and 70% relative humidity.

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Connections 1, 3, 4,7, 8, 10, 13, 20 and 21 are welcome Example 1 showed a positive effect against Chilo suppressalis in this test.

Example 6

Effect against Lucilia sericata

2 ml of an aqueous solution containing 1, 2, 4, 8 or 16 ppm of the compound to be tested were added to 2 ml of a culture medium and then about 30 freshly hatched larvae of the species Lucilia sericata are placed on it. After another 48 hours the insecticidal effect was determined by determining the mortality rate.

Compounds according to Example 1, in particular the compounds 1 to 10, 15 to 17, 19, 21 and 30 to 32 showed a good effect against Lucilia sericata larvae in the above test.

Example 7

Antifeed effects: Leptinotarsa decemlineata

Two 15 cm high potato thaws were with 25 ml of one Acetone / water mixture containing 0.05% test substance (1: 1) injected.

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

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2 B

The connections 1 Ms 4, 6 Ms 11, 13, 14, 19 Ms 21 and according to Example 1 showed a positive antifouling effect in the above test Action against larvae of the species Leptinotarsa decemlineata.

Example 8

Antifeeding effect: Spodoptera littoralis

Two 15 cm high cotton plants were with 25 ml of a Solution containing 0.1% test substance (acetone / water 1: 1) injected. After drying, 5 larvae of the species Spodoptera littoralis (L3 stage) were per plant put on. A plastic cylinder was placed over the plant and closed with an additional cover. The breed damage was determined after 2 days.

The compounds 4, 6, 7, 8, 13 and 31 according to Example 1 showed a feeding-inhibiting effect against larvae of the species Spodoptera littoralis in the above experiment.

Example 9

Effect against Musca donestica

50 g of freshly prepared CSMA nutrient substrate for maggots were each weighed in beaker and then 5 ok> 2.5 or 0.5 ml of a 1% strength by weight acetone solution of the compound to be tested on the nutrient substrate in the cups. After seeing the substrate, it is left Evaporate acetone for at least 20 hours.

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Then there were 25 one-day maggots per compound and concentration from Musca dotnestica to those containing the N'dhrsubatrat treated in this way Cup given. After the maggots had pupated, the pupae formed were flushed out with water separated from the substrate and deposited in vessels closed with sieve covers.

The pupae flushed out per batch were counted (toxic influence of the active ingredient on maggot development). Then became after 10 days the number of flies hatched from the pupae determined and thus a possible influence on the metabolism

established.

The compounds according to Example 1 showed a positive effect in the experiment above.

Example 10

Action against Ae * of the aegypti larvae

There was such an amount of a 0.1% strength acetone solution of the Compound to be tested using a pipette on the surface of 150 ml VJasser in a beaker given that concentrations of 10, 5 and 1 ppm. were obtained. After evaporation of the acetone, 30 to 40 two-day larvae of Ab "des aegypti., In each of the beakers filled with the test solution was inserted. There were 2 beakers per concentration of the test substance used. Ground food was then placed in the beakers, which had a copper gauze lid were covered.

After 1, 2 and 5 days, any mortality was checked. Subsequently, disorders of pupation, metamorphosis and adult moult are evaluated.

The compounds 1, 2, 6, 7, 8, 10, 13, 20 and 31 according to Example 1 showed a good effect against Ab * des aegypti larvae in this test.

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Claims (7)

CIBA-GEIGY AG ' Claims \ .j compounds of the formula I. CO-NH-R ₃ (D R, a methyl or ethyl group and R_ a C, -C, -alkyl or allyl group and R is a substituted phenyl group of the formula R, a halogen atom or a methyl or Trifluoromethyl group and R, a hydrogen or halogen atom or a Represent methyl or trifluoromethyl group, and their tantomeres. 709847/0828 ORIGiNAL INSPECTED CfBA-GEIGYAG -H- 2. Compounds according to claim 1, wherein R / is a chlorine, iodine or bromine atom or a Trifluoromethyl group and R ₁ - represent a hydrogen, chlorine, iodine or bromine atom or a methyl or trifluoromethyl group. 3. Compounds according to claim 1, wherein R- for a 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3-trifluoromethylphenyl-, 4-trifluoromethylphenyl-, 3,5-bis-trifluoromethylphenyl-, 3-chloro-4-trifluoromethylphenyl-, 4-chloro-3-trifluoromethylpheny1- or 4-chloro-2-methylphenyl group. 4. Compounds according to any one of claims 1 to 3, wherein R _? means a methyl, ethyl or isopropyl group. 5. Compounds according to any one of claims 1 to 3, wherein R _? represents an isobutyl or allyl group. 6. 5- (4-chlorophenyl) carbamoyl-1,3-dimethylbarbituric acid according to claim 4. 7. 5- (2,4-dichlorophenyl) carbamoyl-1,3-dimethyl barbituric acid according to claim 4. 7u9ö47 / U828 CIBA-GEIGYAG _> q _ 8. 5-CA-chloro-3-trifluoromethylphenyl) carbamoyl-1,3- -dimethylbarhituric acid according to claim 4. 9. 5- (4-TrifluoromethylphenyI) -carbamoy1-1,3-dime thy 1- barbituric acid according to claim 4. 10. 5- (3-Trifluoromethylphenyl) -carbamoyl-1,3-dimethyl- barbituric acid according to claim 4. 11. 5- (3,5-BistrifluoromethylphenyI) -carbamoy1-1,3- dimethyl barbituric acid according to claim 4. 12. 5- (4-bromophenyl) -carbamoyl-1,3-dimethyl-barbiturates according to claim 4. 13th 5- (4-iodophenyl) -carbamoyl-1,3-dimethylbarbituric acid according to claim 4. 14. 5- (4-Fluorophenyl) -carbamoyl-1,3-dimethylbarbituric acid according to claim 4. 15. 5- (3,4-DichlorophenyI) -carbamoy1-1,3-dimethy1- barbituric acid according to claim 4. 16. 5- (4-chloro-2-methylphenyl) -carbamoyl-1,3-dimethyl- barbituric acid according to claim 4. 17. 5- (3-chloro-4-trifluoromethylpheny1) -carbamoy1-1,3- dimethyl barbituric acid according to claim 4. } ■ 18. 5- (4-chlorophenyl) -carbamyol-1,3-diethylbarbituric acid according to claim 4. 70 9847/0828 11 329 CiBA-QEIGY AG ^ 19. 5- (2,4-dichlorophenyl) -carbamoy 1-1,3-diethyl- barbituric acid according to claim 4. 20. 5- (4-Brompheny1) -carbamoy1-1,3-diethy1-barbituric acid according to claim 4. 21. 5- (4-Chloro-3-Trifluorraethylphenyl) -carbamoyl-1- -methyl-3-ethylbarbituric acid according to claim 22. 5- (4-bromophenyl) -carbamoyl-1-methyl-3-ethyl- barbituric acid according to claim 4. 23. 5- (2,4-dichlorophenyl) -carbamoyl-1-methyl-3-ethyl- barbituric acid according to claim 4. 24. 5- (3-Trifluoromethylphenyl) -carbamoy1-1-methyl-3- ethyl barbituric acid according to claim 25. 5- (4-chlorophenyl) carbamoyl-1-methyl-3-isopropyl- -barbituric acid according to claim 4. 26. 5- (2,4-Dichlorophenyl) -carbamoy1-1-methyl-3-isopropylbarbituric acid according to claim 27. 5- (4-bromophenyl) -carbamoyl-1-methyl-3-isopropyl- -barbitursMure according to claim 4. 28. 5- (4-Trifluoromethylphenyl) -carbamoyl-1,3-diethyl- -barbituric acid according to claim 4. 29. 5- (3,5-Bistrifluoromethylphenyl) -carbamoyl-1,3 diethylbarbituric acid according to claim 709847/0828 CtDA-GElGYAG - 25 - 30. 5- (4-bromophenyl) -carbamoy1-1-methy1-3-isobuty1- barbituric acid according to claim 5. 31. 5- (2,4-Dichlorophenyl) -carbamoyl-1-methyl-3-isobutylbarbituric acid according to claim 32. 5- (3-trifluoromethylphenyI) -carbamoy1-1-methyl- -3-isobutyl-barbituric acid according to claim 33. 5- (4-TrifluoromethylphenyI) -carbamoy1-1-methyl-3- -isobutylbarbituric acid according to claim 34. 5- (4-bromophenyl) -carbamoyl-1-methyl-3-allyl-barbituric acid according to claim 5. 35. 5- (2 _> 4-dichlorophenyl) -carbamoyl-1-methyl-3-allyl-barbituric acid according to claim 5. 36. 5- (3-Trifluoromethylphenyl) -carbamoyl-1-methyl-3- allyl barbituric acid according to claim 37. 5- (4-Trifluoromethylpheny1) -carbamoy1-1-methyl-3- allyl barbituric acid according to claim 38. Process for the preparation of compounds of the formula I according to claim 1, characterized in that that he a) an ester of the formula II COOR ₄ "W" " ^R 1 N / ^R 2 709847/0828 CIBA-GE (GY AG .w - / η) - reacts with an aniline of the formula III R _{3 —NH 2} (III); b) a compound of the formula IV (IV) with an isocyanate of the formula V R ₃ —N = CO (γ) let react; or that one c) a compound of the above formula IV with an azide of the formula VI R ₃ —CO-N ₃ (VI) treated; where in the formulas II to VI R. to R-die have already given meanings in claim 1 and R 1 stands for a C 1 -C 4 -alkyl group. 39. Insecticidal agent containing as active component a compound according to any one of claims 1 to 709847/0828 40. Using a connection according to one of the
Claims 1 to 37 for combating insects. 41. Use according to claim 40 for combating insects which are harmful to plants. 42. Use according to claim 41 for controlling plant-damaging insects in cotton or fruit crops. 43. Use according to claim 42 for combating insects of the order Colleoptera. 44. Use according to claim 43 for combating insects of the species Leptinotarsa decemlineata or
Anthonomus grandis. 45. Use according to claim 40 for combating ectoparasitic insects in farm animals. 46. Use according to claim 45 for combating insects of the order Diptera. 47. Use according to claim 46 for combating insects of the genus Lucilia. 48. Use according to claim 47 for combating insects of the species Lucilia sericata. 7 0 9847/0828